A Reactivity/Affinity Switch for Parallel Kinetic Resolution: α-Amino Acid Quasienantiomers and the Resolution of Cyclopropene Carboxylic Acids

Journal of the American Chemical Society

Volumn 126, Issue 14, 2004, Pages 4490-4491

  Liao, Lian An ^a   Zhang, Fan ^a   Dmitrenko, Olga ^a   Bach, Robert D ^a   Fox, Joseph M ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; CARBOXYLIC ACID; CYCLOALKENE; CYCLOPROPENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHIRALITY; CHROMATOGRAPHY; CYCLOPROPENATION; DENSITY FUNCTIONAL THEORY; ENANTIOMER; STEREOCHEMISTRY;

AMINO ACIDS; CARBOXYLIC ACIDS; CYCLOPROPANES; KINETICS; STEREOISOMERISM; THERMODYNAMICS;

EID: 1842738716     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049779t     Document Type: Article

References (19)

1. (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584.
2. (b) Eames, J. Angew. Chem., Int. Ed. 2000, 39, 885.
3. (c) Delhi, J. R.; Gotor, V. Chem. Soc. Rev. 2002, 31, 365.
4. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley & Sons: New York, 1994; pp132-134 and 1205.
5. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
6. (a) Vedejz, E.; Rozners, E. J. Am. Chem. Soc. 2001, 123, 2428.
7. (b) Al-Sehemi, A. G.; Atkinson, R. S.; Meades, C. K. Chem. Commun. 2001, 2684.
8. (a) Liao, L.-a.; Fox, J. M. J. Am. Chem. Soc. 2002, 124, 14322 and references therein.
9. (b) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295
10. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198.
11. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566.
12. Protopopova, M. N.; Shapiro, E. A. Russ. Chem. Rev. (Engl. Transl.) 1989, 58, 667.
13. For nonracemic cyclopropenes, see ref 9. Lead references for enantioselective cyclopropenation: (a) Doyle, M. P.; Protopopova, M.; Müller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492.
14. (b) Doyle, M. P.; Ene, D. G.; Peterson, C. S.; Lynch, V. Angew. Chem., Int. Ed. 1999, 38, 700.
15. (c) Müller, P.; Imogaï, H. Tetrahedron: Asymmetry 1998, 9, 4419.
16. 4 can induce high enantioselectivities in the formation of cyclopropenes with quaternary centers: Huw Davies, personal communication.
17. (a) Liao, L.-a.; Zhang, F.; Yan, N.; Golen, J. A.; Fox, J. M. Tetrahedron 2004, 60, 1803.
18. (b) Fox, J. M.; Dmitrenko, O.; Liao, L.-a.; Bach, R. D. submitted and references therein.
19. (c) Williams, A. Acc. Chem. Res. 1989, 22, 387.