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

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

doi:10.1039/b401293c

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

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	1128-1129
Number of pages	2
Journal	Chemical Communications
Volume	4
Issue number	9
DOIs	https://doi.org/10.1039/b401293c
Publication status	Published - 1 Jan 2004

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title = "Double asymmetric induction as a mechanistic probe: conjugate addition for the asymmetric synthesis of a pseudotripeptide",

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.",

author = "Davies, {Stephen G.} and Hermann, {Gesine J.} and Sweet, {Miles J.} and Smith, {Andrew D.}",

year = "2004",

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doi = "10.1039/b401293c",

language = "English",

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pages = "1128--1129",

journal = "Chemical Communications",

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TY - JOUR

T1 - Double asymmetric induction as a mechanistic probe

T2 - conjugate addition for the asymmetric synthesis of a pseudotripeptide

AU - Davies, Stephen G.

AU - Hermann, Gesine J.

AU - Sweet, Miles J.

AU - Smith, Andrew D.

PY - 2004/1/1

Y1 - 2004/1/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=2442710051&partnerID=8YFLogxK

U2 - 10.1039/b401293c

DO - 10.1039/b401293c

M3 - Article

AN - SCOPUS:2442710051

SN - 1359-7345

VL - 4

SP - 1128

EP - 1129

JO - Chemical Communications

JF - Chemical Communications

IS - 9

ER -

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

Abstract

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