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University of Pennsylvania             Department of Chemistry

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Kozlowski Group Publications

 

87) Peacock, J. R.; Walvoord, R. R.; Chang, A. Y.; Kozlowski, M. C.; Ga,per, H.; Hou, Y.-M. “Amino Acid-Dependent Stability of the Acyl Linkage in Aminoacyl-tRNA.” RNA. 2014, accepted.

86) Regalado, E. L.; Kozlowski, M. C.; Curto, J. M.; Berritt, S.; Ritter, T.; Campbell, M.; Mazzotti, A.; Hamper, B.; Spilling, C. D.; Mannino, M. P.; White, C. W.; Howell, J. L.; Liu, J.; Welch, C. J. “Support of Academic Synthetic Chemistry using Advanced Separation Technologies from the Pharmaceutical Industry.” Org. Biomol. Chem. 2014, accepted.

85) Walvoord, R. R.; Kozlowski, M. C. “Minimizing the Amount of Nitromethane in Palladium Catalyzed Cross Coupling with Aryl Halides.” J. Org. Chem. 2013, 78, 8859–8864. DOI PMC3778657

84) Padilla-Salinas, R.; Walvoord, R. R.; Tcyrulnikov, S.; Kozlowski, M. C. “Nitroethylation of Vinyl Triflates and Bromides.” Org. Lett. 2013,15, 3966–3969. DOI PMC3775651

83) Barkallah, S.;.Kozlowski, M. C. "Studies on Chirality Transfer Through Hydrogen Bonding in Strecker Reaction: The Case for Amino Acids" J. Soc. Chem. Tunisie. 2013in press

82) Allen, S. E.; Walvoord, R. R.; Padilla-Salinas, R.;Kozlowski, M. C. "Aerobic Copper-Catalyzed Organic Reaction" Chem. Rev. 2013113, 6234–6438. DOI PMID: 23786461

81)  Dickstein, J. S.; Curto, J. M.; Gutierrez, O.; Mulrooney, C. A.; Kozlowski, M. C. "Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps" J. Org. Chem. 201378, 4744-4761. DOI PMC3686493

80)  Podlesny, E. E.; Kozlowski, M. C. "A Divergent Approach to the Bisanthraquinone Natural Products: Total Synthesis of (S)-Bisoranjidiol and Derivatives from Binaphtho-para-quinones" J. Org. Chem. 201378, 466-476. DOI PMC3560291

79)  Metz, A. E.; Kozlowski, M. C. "2-Aryl-2-nitroacetates as Central Precursors to Aryl Nitromethanes, alpha-Ketoesters, and alpha-Amino Acids" J. Org. Chem. 2013, 78, 717-722 . DOI PMC3548967

78)   Cao, T.; Linton, E. C.; Deitch, J.; Berritt, S.; Kozlowski, M. C. "Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary Oxindoles and Spirocyclic Lactones" J. Org. Chem. 201377, 11034-11055. DOI

77) Huynh, P. N. H.; Walvoord, R. R.; Kozlowski, M. C. "Rapid Quantification of the Activating Effects of Hydrogen Bonding Catalysts with a Calorimetric Sensor." J. Am. Chem. Soc., 2012, 134, 15621-15623. DOI

76) Podlesny, E. E.; Carroll, P. J.; Kozlowski, M. C.“Selective Oxidation of 8,8'-Hydroxylated Binaphthols to Bis-spironaphthalenones or Binaphto-para- and Binaphto-ortho-quinones.” Org. Lett. 2012, 14, 4862-4865. DOI

75) Mulrooney, C. A.; O'Brien, E. M.; Morgan, B. J.; Kozlowski, M. C.“Perylenequinones: Isolation, Synthesis and Biological Activity.” Eur. J. Org. Chem. 2012, 21, 3887-3904. DOI

74) Walvoord, R. R.; Berritt, S.; Kozlowski, M. C. “Palladium-Catalyzed Nitromethylation of Aryl Halides: An Orthogonal Formylation Equivalent.” Org. Lett. 2012, 14, 4086-4089. DOI

73)   Allen, S. E.; Mahatthananchai, J.; Bode, J. W.; Kozlowski, M. C. “Oxyanion-Steering and CH-π Interactions as Key Elements in a N-Heterocyclic Carbene-Catalyzed [4+2] Cycloaddition.” J. Am. Chem. Soc. 2012, 134, 12098–12103. DOI

72)   Podlesny, E. E.; Kozlowski, M. C. “Structural Reassignment of a Marine Metabolite from a Binaphtalenetetrol to a Tetrabrominated Diphenyl Ether.” J. Nat. Prod. 2012, 75, 1125–1129. DOI

71)   Podlesny, E. E.; Kozlowski, M. C. “Enantioselective Total Synthesis of (S)-Bisoranjidiol, an Axially Chiral Bisanthraquinone” Org. Lett. 2012, 14, 1408–1411. DOI

70)   Metz, A. E.; Berritt, S.; Dreher, S. D.; Kozlowski, M. C. “Efficient Palladium-Catalyzed Cross-Coupling of Highly Acidic Substrates, Nitroacetates” Org. Lett. 2012, 14, 760–763. DOI

69)   Cao, T.; Deitch, J.; Linton, E. C.; Kozlowski, M. C. “Catalytic Enantioselective Saucy-Marbet Claisen Rearrangement:  Asymmetric Synthesis of Allenyl Oxindoles and Spirooxindoles” Angew. Chem. Int. Ed. 201251, 2448–2451. DOI (Synfacts highlight)

68)   Lowell, A. N.; Fennie, M. W.; Kozlowski, M. C. "Alternative spiroketalization methods toward purpuromycin: A diketone approach to prevent benzofuran formation" J. Org. Chem. 201176, 6488–6502. DOI

67)   Bandichhor, R.; Lowell, A. N.; Kozlowski, M. C. "Alternative spiroketalization methods toward purpuromycin: A hemiketal conjugate addition strategy and use of an electron rich isocoumarin precursor" J. Org. Chem. 2011, 76, 6475–6487. DOI

66)   Kaeobamrung, J.; Kozlowski, M. C.; Bode, J. W. "Chiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from α,β-unsaturated aldehydes for enantioselective Diels-Alder reactions" Proc. Nat. Acad. Sci. 2010, 107, 20661–20665. DOI

65)   Lowell, A. N.; Wall, P. D.; Waters, S. P.; Kozlowski, M. C. “Syntheses of Differentially Protected Isocoumarins” Tetrahedron 2010, 66, 5573-5582. DOI

64)   Kozlowski, M. C., Ianni, J. C. “Quantum Molecular Interaction Field Models of Substrate Enantioselection in Asymmetric Processes” J. Mol. Cat. A 2010, 324, 141-145. DOI

63)   O’Brien, E. M.; Li, J.; Carroll, P. J.; Kozlowski, M. C. “Synthesis of the Cores of Hypocrellin and Shiraiachrome: Diastereoselective 1,8-Diketone Aldol Cyclization” J. Org. Chem. 2010, 75, 69-73. DOI

62)   O’Brien, E. M.; Morgan, B. J.; Mulrooney, C. A.; Kozlowski, M. C.  “Perylenequinone Natural Products: Total Synthesis of Hypocrellin A” J. Org. Chem. 2010, 75, 57-68. DOI

61)   Morgan, B. J.; Mulrooney, C. A.; Kozlowski, M. C.  “Perylenequinone Natural Products:  Evolution of the Total Synthesis of Cercosporin” J. Org. Chem. 2010, 75, 44-56. DOI

60)   Morgan, B. J.; Mulrooney, C. A.; O’Brien, E. M.; Kozlowski, M. C.  “Perylenequinone Natural Products:  Total Syntheses of the Diastereomers (+)-Phleichrome and (+)-Calphostin D by Assembly of Centrochiral and Axial Chiral Fragments” J. Org. Chem. 2010, 75, 30-43. DOI

59)   Mulrooney, C. A.; Morgan, B. J.; Li, X.; Kozlowski, M. C.  “Perylenequinone Natural Products:  Asymmetric Synthesis of the Oxidized Pentacyclic Core” J. Org. Chem. 2010, 75, 16-29. DOI

58)   Kozlowski, M. C.; Morgan, B. J.; Linton, E. C.; “Total Synthesis of Chiral Biaryl Natural Products by Asymmetric Biaryl Coupling” Chem. Soc. Rev. 2009, 38, 3193-3207. DOI

57)   Morgan, B. J.; Dey, S.; Johnson, S. W.; Kozlowski, M. C. “Total Synthesis of Cercosporin and New Photodynamic Perylenequinones:  Inhibition of the Protein Kinase C Regulatory Domain” J. Am. Chem. Soc.  2009131, 9413–9425. DOI

56)   Wentzel, M. T.; Kamble, R.; Wall, P.; Hewgley, J. B.; Kozlowski, M. C. “Copper Catalyzed N-Arylation of Hindered Substrates Under Mild Conditions” Adv. Synth. Cat. 2009351, 931-937. DOI

55)   Annamali, R.; Linton, E. C.; Kozlowski, M. C. “Design of an Organocatalytic Claisen Rearrangement Catalyst for Monodentate Substrates” Org. Lett. 2009, 11, 621-624. DOI

54. Dugan, E. C.; Kozlowski, M. C. “Catalytic Enantioselective Meerwein-Eschenmoser Claisen Rearrangement:  Asymmetric Synthesis of Allyl Oxindoles” J. Am. Chem. Soc. 2008, 130, 16162–16163. DOI

53. Joshua S. Dickstein, J. S.; Norman, A.; Fennie, Michael W.; Jennifer, B.; Kozlowski, M. C. “Three Component Coupling of a-Iminoesters via Umpolung Addition of Organometals: Synthesis of a,a-Disubstituted a-Amino Acids” J. Am. Chem. Soc. 2008, 130, 15794–15795. DOI

52. Hewgley, J. B.; Stahl, S. S.; Kozlowski, M. C. “Mechanistic Study of Asymmetric Oxidative Biaryl Coupling: Evidence for Self-Processing of the Copper Catalyst to Achieve Control of Oxidase vs. Oxygenase Activity” J. Am. Chem. Soc. 2008, 130, 12232-12233. DOI

51. O’Brien, E. M.; Morgan; B. J.; Kozlowski, M. C. “Dynamic Sterochemistry Transfer in a Transannular Aldol Reaction: Total Synthesis of Hypocrellin A” Angew. Chem., Int. Ed. 2008, 47, 6877-6880. Highlighted in Chemistry World: Chemistry World DOI

50. Dickstein, J. S.; Kozlowski, M. C. “Organometal Additions to α-Iminoesters: N-Alkylation via Umpolung” Chem. Soc. Rev. 2008, 37, 1166-1173. DOI

49. Lowell, A. N.; Fennie, M. W.; Kozlowski, M. C. “A Concise Synthesis of the Naphthalene Portion of Purpuromycin” J. Org. Chem. 2008, 73, 1911-1918. DOI

48. Dickstein, J. S.; Mulrooney, C. A.; O’Brien, E. M.; Morgan; B. J.; Kozlowski, M. C. “Development of a Catalytic Aromatic Decarboxylation Reaction” Org. Lett. 2007, 9, 2441-2444. “Top 20 Most Accessed Articles April-June 2007” DOI

47. Morgan, B. J.; Xie, X.; Phuan, P-W.; Kozlowski, M. C. “Enantioselective Synthesis of Binaphthyl Polymers using Chiral Asymmetric Phenolic Coupling Catalysts: Oxidative Coupling and Tandem Glaser/Oxidative Coupling” J. Org. Chem. 2007, 72, 6171-6182. DOI

46. Morgan, B. J.; Kozlowski, M. C. “(5S)-2,2,3-Trimethyl-5-(phenylmethyl)-4-imidazolidinone” EROS, Article Online Posting Date: March 14, 2008 DOI

45. Kozlowski, M. C., Dugan, E. C.; DiVirgilio, E. S.; Maksimenka, K.; Bringmann, G. “Asymmetric Total Synthesis of Nigerone and ent-Nigerone: Enantioselective Oxidative Biaryl Coupling of Highly Hindered Naphthols” Adv. Synth. Cat. 2007, 349, 583-594; invited contribution to “M. Shibasaki 60th Birthday Dedicated Issue” DOI

44. DiVirgilio, E. S.; Dugan, E. C.; Mulrooney, C. A.; Kozlowski, M. C. “Asymmetric Total Synthesis of Nigerone” Org. Lett. 2007, 9, 385-388.DOI

43. Waters, S. P.; Fennie, M. W.; Kozlowski, M. C. “Investigation of a Convergent Route to Purpuromycin: Benzofuran Formation vs Spiroketalization” Org. Lett. 2006, 8, 3243-3246. DOI

42.Waters, S. P.; Kozlowski, M. C. “Convergent Route to the Purpuromycin Bisphenolic Spiroketal: Hydrogen Bonding Control of Spiroketalization Stereochemistry” Tetrahedron. Lett. 2006, 47, 5409-5413.DOI

41. Morgan, B. J.; Kozlowski, M. C. “(–)-Sparteine” EROS, Article Online Posting Date: March 15, 2007. DOI

40. Basra, S.; Fennie, M. W.; Kozlowski, M. C. “Catalytic Asymmetric Addition of Dialkylzincs to a-Aldiminoesters” Org. Lett. 2006, 8, 2659-2662.DOI

39. Huang, J.; Ianni, J. C.; Antoline, J. E.; Hsung, R. P; Kozlowski, M. C. “De Novo Chiral Amino Alcohols in Catalyzing Asymmetric Additions to Aryl Aldehydes” Org. Lett. 2006, 8, 1565-1568. DOI

38. Ianni, J. C.; Annamalai, V.; Phuan, P.-W.; Kozlowski, M. C. “A Priori Theoretical Prediction of Selectivity in Asymmetric Catalysis: Design of New Chiral Catalysts using Quantum Molecular Interaction Fields” Angew. Chem., Int. Ed. 2006, 45, 5502-5505. DOI

37. Kozlowski, M. C.; Kamble, R. “1,5-Diaza-cis-decalin” e-EROS, Article Online Posting Date: September 15, 2006. DOI

36. Kozlowski, M. C.; DiVirgilio, E. S.; Malolanarasimhan, K.; Mulrooney, C. A. “Oxidation of Chiral a-Phenylacetate Derivatives: Formation of Dimers with Contiguous Quaternary Stereocenters versus Tertiary Alcohols” Tetrahedron: Asymmetry 2005, 16,3599-3605; invited contribution to "Asymmetric Oxidations" Symposium-in-Print. DOI

35. Fennie, M. W.; DiMauro, E. F.; O’Brien, E. M.; Annamalai, V.; Kozlowski, M. C. “Mechanism and Scope of Salen Bifunctional Catalysts in Asymmetric Aldehyde and a-Ketoester Alkylation” Tetrahedron 2005, 61, 6249-6265; invited contribution to "Catalysis in Industry and Academia" Symposium-in-Print.  DOI

34. Phuan, P.-W.; Ianni, J. C.; Kozlowski, M. C. "Is the A-Ring of Sparteine Essential for High Enantioselectivity in the Asymmetric Lithiation-Substiution of N-Boc-pyrrolidine?" J. Am. Chem. Soc. 2004, 126, 15473-15479. DOI

33. Lipkowitz, K. B.; Kozlowski, M. C. "Understanding Stereoinduction in Catalysis via Computer: New Tools for Asymmetric Synthesis" Synlett 2003, 1547-1565. DOI

32. Li, X.; Hewgley, J. B.; Mulrooney, C.; Yang, J.; Kozlowski, M. C. "Enantioselective Oxidative Biaryl Coupling Reactions Catalyzed by 1,5-Diazadecalin Metal Complexes:  Efficient Formation of Chiral Functionalized BINOL Derivatives" J. Org. Chem. 2003, 68, 5500-5511. DOI

31. Mulrooney, C. A.; Li, X.; DiVirgilio, E. S.; Kozlowski, M. C. "General Approach for the Synthesis of Chiral Perylenequinones via Catalytic Enantioselective Oxidative Biaryl Coupling" J. Am. Chem. Soc. 2003, 125, 6856-6857. DOI

30. Kozlowski, M. C.; Dixon, S.; Panda, M.; Lauri, G. "Quantum Mechanical Models Correlating Structure with Selectivity: Predicting the Enantioselectivity of b-Amino Alcohol Catalysts in Aldehyde Alkylation" J. Am. Chem. Soc. 2003, 125, 6614-6615. DOI

29. Xie, X.; Phuan, P.-W.; Kozlowski, M. C. "Novel Pathways for the Formation of Chiral Binaphthyl Polymers:  Oxidative Asymmetric Phenolic Coupling and Tandem Glaser/Oxidative Asymmetric Phenolic Coupling" Angew. Chem., Int. Ed. 2003, 42, 2168-2170. DOI

28. Phuan, P.-W.; Kozlowski, M. C. "2.15.8 Product Class 8: Naphthyridines" in Category 2: Hetarenes and Related Ring Systems Volume 15: Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom, Science of Synthesis, Thieme: New York, 2004.

27. Kozlowski, M. C.; Panda, M. "Computer-Aided Design of Chiral Ligands.  Part II.  Functionality Mapping as a Method to Identify Stereocontrol Elements for Asymmetric Reactions" J. Org. Chem. 2003, 68, 2061-2076. Featured on the cover, March 21, 2003 (issue #6).  DOI

26. Annamalai, V.; DiMauro, E. F.; Carroll, P. J.; Kozlowski, M. C. "Catalysis of the Michael Addition Reaction by Late Transition Metal Complexes of BINOL-Derived Salens" J. Org. Chem. 2003, 68, 1973-1981. DOI

25. DiMauro, E. F.; Mamai, A.; Kozlowski, M. C. "Synthesis, Characterization, and Metal Complexes of a Salen Ligand Containing a Quinoline Base" Organometallics 2003, 22, 850-855. DOI

24. Smith, A. B., III.; Lee, D.; Adams, C. M.; Kozlowski, M. C. "SmI2-Promoted Oxidation of Aldehydes in the Presence of Electron Rich Heteroatoms"  Org. Lett. 2002, 4, 4539-4541. DOI

23. Kozlowski, M. C.; Waters, S. P.; Skudlarek, J. W.; Evans, C. A. "Computer-Aided Design of Chiral Ligands. Part III.  A Novel Ligand for Asymmetric Allylation Designed Using Computational Techniques" Org. Lett. 2002, 4, 4391-4393. DOI

22. Panda, M.; Phuan, P.-W.; Kozlowski, M. C. "Theoretical and Experimental Studies of Asymmetric Organozinc Additions to Benzaldehyde Catalyzed by Flexible and Constrained g-Aminoalcohols" J. Org. Chem. 2003, 68, 564-571. DOI

21. DiMauro, E. F.; Kozlowski, M. C. "The First Catalytic Asymmetric Addition of Dialkylzincs to a-Ketoesters" Org. Lett. 2002, 4, 3781-3784. DOI

20. DiMauro, E. F.; Kozlowski, M. C. "Development of Bifunctional Salen Catalysts: Rapid, Chemoselective Alkylations of a-Ketoesters" J. Am. Chem. Soc. 2002, 124, 12668-12669. DOI

19. Kozlowski, M. C.; Li, X.; Carroll, P. J.; Xu, Z. "Copper(II) Complexes of Novel 1,5-Diaza-cis-decalin Diamine Ligands:  An Investigation of Structure and Reactivity" Organometallics 2002, 21, 4513-4522. DOI

18. Panda, M.; Phuan, P.-W. Kozlowski, M. C. "Utility of Calculated 13C NMR Chemical Shifts in Differentiating Conformational Isomers:  A Study of Metal-Complexed and Uncomplexed Bispidines" Chem. Commun. 2002, 1552-1553. DOI

17. Phuan, P.-W.; Kozlowski, M. C. "Control of the Conformational Equilibria in Aza-cis-Decalins: Structural Modification, Solvation, and Metal Chelation " J. Org. Chem. 2002, 67, 6339-6346. DOI

16. Li, X.; Xu, Z.; DiMauro, E. F.; Kozlowski, M. C. "Unusual Oxidative Rearrangement of 1,5-Diazadecalin"  Tetrahedron Lett. 2002, 43, 3747-3750. DOI

15. Xu, Z.; Kozlowski, M. C. "Conformational Control of Flexible Molecules: Design and Synthesis of Novel Chiral 1,5-Diaza-cis-decalins" J. Org. Chem. 2002, 67, 3072-3078. DOI

14. Kozlowski, M. C.; Panda, M. "Computer-Aided Design of Chiral Ligands. Part I.  Database Search Methods to Identify Chiral Ligand Types for Asymmetric Reactions" J. Mol. Graphics Modell. 2002, 20, 399-409. DOI

13. DiMauro, E. F.; Kozlowski, M. C. "Late Transition Metal Complexes of BINOL-Derived Salens:  Synthesis, Structure, and Reactivity" Organometallics 2002, 21, 1454-1461. DOI

12. DiMauro, E. F.; Kozlowski, M. C. "Phosphabenzenes as Electron Withdrawing Ligands in Catalysis"  J. Chem. Soc., Perkin Trans. I 2002, 439-444.  DOI

11. DiMauro, E. F.; Kozlowski, M. C. "Salen-Derived Catalysts Containing Secondary Basic Groups in the Addition of Diethylzinc to Aldehydes"  Org. Lett. 2001, 3, 3053-3056.  DOI

10. Xie, X.; Kozlowski, M. C. "Synthesis of the Naphthalene Portion of the Rubromycins"  Org. Lett. 2001, 3, 2661-2663. DOI

9. Xie, X.; Freed, D. A.; Kozlowski, M. C. "Synthesis and Conformational Properties of N-Monoalkyl 1,5-Diaza-cis-decalins"  Tetrahedron Lett.  2001, 42, 6451-6454.  DOI

8. Phuan, P.-W.; Kozlowski, M. C. "Convenient Preparation of Naphthyridines from Halopyridines:  Sequential Heck Coupling and Cyclization"  Tetrahedron Lett. 2001, 42, 3963-3965.  DOI

7. DiMauro, E. F.; Kozlowski, M. C. "BINOL-Salen Metal Catalysts Incorporating a Bifunctional Design"  Org. Lett. 2001, 3, 1641-1644.  DOI

6. Freed, D. A.; Kozlowski, M. C. "N-Acyl Imine and Enamide Intermediates in Palladium-Catalyzed Amidocarbonylation Reaction" Tetrahedron Lett. 2001, 42, 3403-3406. DOI

5. Waters, S. P.; Kozlowski, M. C. "Synthesis of the Isocoumarin Portion of the Rubromycins"  Tetrahedron Lett. 2001, 42, 3567-3570. DOI

4. Kozlowski, M. C.; Xu, Z.; Santos, A. G. "Synthesis and Conformational Analysis of 2,6-Dimethyl-1,5-diaza-cis-decalins" Tetrahedron 2001, 57, 4537-4542. DOI

3. Li, X.; Yang, J.; Kozlowski, M. C. "Enantioselective Oxidative Biaryl Coupling Reactions Catalyzed by 1,5-Diazadecalin MetalComplexes" Org. Lett. 2001, 3, 1137-1140. DOI

2. Ganguly, B.; Freed, D. A.; Kozlowski, M. C. "Relevance of Torsional Effects to the Conformational Equilibria of 1,5-Diaza-cis-decalins:  A Theoretical and Experimental Study"  J. Org. Chem. 2001, 66, 1103-1108. DOI

1. Li, X.; Schenkel, L. B.; Kozlowski, M. C. "Synthesis and Resolution of a Novel Chiral Diamine Ligand and Application to Asymmetric Lithiation-Substitution"  Org. Lett. 2000, 2, 875-878. DOI