Journal of Organic Chemistry p. 5011 - 5015 (1995)
Update date:2022-08-04
Topics:
Collado, Ivan
Ezquerra, Jesus
Pedregal, Concepcion
Alkylation of nonracemic N-acyliminium ions derived from proline and 4-substituted prolines has been extended to different types of Grignard-derived organocopper reagents.The reaction proceeds with high yield and stereoselectivity to yield 5-mono- and 4,5-disubstituted prolinates.The stereochemistry is controlled by the formation of a RCu-? complex intermediate between the N-acyliminium ion, the carbonyl group of the ester, and the copper species.
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