Double asymmetric induction as a mechanistic probe: conjugate addition for the asymmetric synthesis of a pseudotripeptide

Literature Information

Publication Date 2004-04-08
DOI 10.1039/B401293C
Impact Factor 6.222
Authors

Stephen G. Davies, Gesine J. Hermann, Miles J. Sweet, Andrew D. Smith


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Abstract

Double asymmetric induction as a mechanistic probe indicates that, for the conjugate addition of (R)- and (S)-lithium N-benzyl-N-α-methylbenzylamide to (S)-3′-phenylprop-2′-enoyl-4-benzyloxazolidinone, the reactive conformation of the N-acyl oxazolidinone is the anti-s-cis form, facilitating the asymmetric synthesis of a pseudotripeptide.

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