A memory of chirality approach to the stereoselective synthesis of 4-hydroxy-α-methylprolines

Organic Letters

Volumn 9, Issue 16, 2007, Pages 3028-3032

  Kolaczkowski, Lawrence ^a   Barnes, David M ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; PROLINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PROLINE; STEREOISOMERISM;

EID: 34547960784     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071023m     Document Type: Article

References (24)

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20. 4 The trans stereochemistry of the major product (14) was confirmed by removal of the benzyl ester and single-crystal X-ray analysis of the resultant N-boc-4-hydroxy-α-methylproline (21).
21. Metal-halogen exchange induced cyclization of tu-iodopentyl epoxides led predominately to the cyclobutylmethanol. Addition of certain Lewis acids reverses selectivity to the cyclopentanol. See: Cooke, M. P.; Houpis, I. N. Tetrahedron Lett. 1985, 26, 3643-3646.
22. Reaction of ω-bromopentyl epoxides with activated copper in the presence of trialkyl or triaryl phosphines leads predominately to the cyclopentanols. See: Wu, T.-C.; Rieke, R. D. Tetrahedron Lett. 1988, 29, 6753-6756.
23. See also: Stork, G.; Cohen, J. F. J. Am. Chem. Soc. 1974, 96, 5270-5272.
24. During the review process an alternate mechanism was proposed in which the asymmetric alkylation results from kinetic resolution of racemic enolates by the alkoxide derived from the chiral chlorohydrin. We thank the referee for this suggestion.