Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: a mechanistic probe

Stephen G. Davies; Ai M. Fletcher; Gesine J. Hermann; Giovanna Poce; Paul M. Roberts; Andrew D. Smith; Miles J. Sweet; James E. Thomson; Andrew David Smith

doi:10.1016/j.tetasy.2010.03.033

Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: a mechanistic probe

Stephen G. Davies
, Ai M. Fletcher
, Gesine J. Hermann
, Giovanna Poce
, Paul M. Roberts
, Andrew D. Smith
, Miles J. Sweet
, James E. Thomson
, Andrew David Smith

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

Abstract

The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The beta-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an alpha,beta,alpha-pseudotripeptide. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1635-1648
Number of pages	14
Journal	Tetrahedron: Asymmetry
Volume	21
Issue number	13-14
DOIs	https://doi.org/10.1016/j.tetasy.2010.03.033
Publication status	Published - 14 Jul 2010

Keywords

PARALLEL KINETIC RESOLUTION
HOMOCHIRAL ALPHA,BETA-UNSATURATED ESTERS
JASPINE-B PACHASTRISSAMINE
PARTIALLY-MODIFIED RETRO
D-LYXO-PHYTOSPHINGOSINE
BETA-AMINO ACIDS
ASYMMETRIC-SYNTHESIS
ORGANOCOPPER REAGENTS
MICHAEL ADDITIONS
ORGANIC-SYNTHESIS

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@article{eef9a4b074e246209792414cc51000ec,

title = "Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: a mechanistic probe",

abstract = "The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The beta-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an alpha,beta,alpha-pseudotripeptide. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "PARALLEL KINETIC RESOLUTION, HOMOCHIRAL ALPHA,BETA-UNSATURATED ESTERS, JASPINE-B PACHASTRISSAMINE, PARTIALLY-MODIFIED RETRO, D-LYXO-PHYTOSPHINGOSINE, BETA-AMINO ACIDS, ASYMMETRIC-SYNTHESIS, ORGANOCOPPER REAGENTS, MICHAEL ADDITIONS, ORGANIC-SYNTHESIS",

author = "Davies, \{Stephen G.\} and Fletcher, \{Ai M.\} and Hermann, \{Gesine J.\} and Giovanna Poce and Roberts, \{Paul M.\} and Smith, \{Andrew D.\} and Sweet, \{Miles J.\} and Thomson, \{James E.\} and Smith, \{Andrew David\}",

year = "2010",

month = jul,

day = "14",

doi = "10.1016/j.tetasy.2010.03.033",

language = "English",

volume = "21",

pages = "1635--1648",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "13-14",

}

TY - JOUR

T1 - Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: a mechanistic probe

AU - Davies, Stephen G.

AU - Fletcher, Ai M.

AU - Hermann, Gesine J.

AU - Poce, Giovanna

AU - Roberts, Paul M.

AU - Smith, Andrew D.

AU - Sweet, Miles J.

AU - Thomson, James E.

AU - Smith, Andrew David

PY - 2010/7/14

Y1 - 2010/7/14

N2 - The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The beta-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an alpha,beta,alpha-pseudotripeptide. (C) 2010 Elsevier Ltd. All rights reserved.

AB - The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The beta-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an alpha,beta,alpha-pseudotripeptide. (C) 2010 Elsevier Ltd. All rights reserved.

KW - PARALLEL KINETIC RESOLUTION

KW - HOMOCHIRAL ALPHA,BETA-UNSATURATED ESTERS

KW - JASPINE-B PACHASTRISSAMINE

KW - PARTIALLY-MODIFIED RETRO

KW - D-LYXO-PHYTOSPHINGOSINE

KW - BETA-AMINO ACIDS

KW - ASYMMETRIC-SYNTHESIS

KW - ORGANOCOPPER REAGENTS

KW - MICHAEL ADDITIONS

KW - ORGANIC-SYNTHESIS

U2 - 10.1016/j.tetasy.2010.03.033

DO - 10.1016/j.tetasy.2010.03.033

M3 - Article

SN - 0957-4166

VL - 21

SP - 1635

EP - 1648

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 13-14

ER -

Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: a mechanistic probe

Abstract

Keywords

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