Efficient method for selective introduction of substituents as C(5) of isoleucine and other α-amino acids

Organic Letters

Volumn 8, Issue 13, 2006, Pages 2819-2821

  Reddy, Leleti Rajender ^a   Reddy, B V Subba ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BROMINATED HYDROCARBON; CHLORINATED HYDROCARBON; ESTER; ISOLEUCINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

AMINO ACIDS; ESTERS; HYDROCARBONS, BROMINATED; HYDROCARBONS, CHLORINATED; ISOLEUCINE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33746108032     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060952v     Document Type: Article

References (17)

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13. +⋯H⋯C hydride abstraction (ca. 90°), in accord with expectations based on orbital interactions.
14. See, for example: Hartman, M. C. T.; Josephson, K.; Szostak, J. W. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 4356-4361.
15. Recent theoretical analyses of C-H abstraction reactions by free radicals indicate that the barrier heights for these processes are lowered in proportion to the electron deficiency (or electron affinity) of the abstracting radical. See: Donahue, N. M.; Clarke, J. S.; Anderson, J. G. J. Phys. Chem. A 1998, 102, 3923-3933. As far as we are aware, this paper describes the first synthetic application and support of this theoretical proposal.
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