Parallel synthesis of homochiral beta-amino acids

Stephen G. Davies; Andrew W. Mulvaney; Angela J. Russell; Andrew D. Smith

doi:10.1016/j.tetasy.2007.06.008

Parallel synthesis of homochiral beta-amino acids

Stephen G. Davies, Andrew W. Mulvaney, Angela J. Russell, Andrew D. Smith

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

49 Citations (Scopus)

Abstract

The parallel asymmetric synthesis of an array of 30 P-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 alpha,beta-unsaturated esters to both enantiomeric series of the corresponding beta-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol. (C) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1554-1566
Number of pages	13
Journal	Tetrahedron: Asymmetry
Volume	18
Issue number	13
DOIs	https://doi.org/10.1016/j.tetasy.2007.06.008
Publication status	Published - 17 Jul 2007

Keywords

SOLID-PHASE SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
ASYMMETRIC-SYNTHESIS
ORGANIC-SYNTHESIS
SMALL MOLECULES
ALDOL REACTIONS
IRON COMPLEXES
LITHIUM AMIDES
DERIVATIVES
LIBRARY

Access to Document

10.1016/j.tetasy.2007.06.008

Cite this

@article{a3059ce8422d4b50af292ac2c22a1fa3,

title = "Parallel synthesis of homochiral beta-amino acids",

abstract = "The parallel asymmetric synthesis of an array of 30 P-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 alpha,beta-unsaturated esters to both enantiomeric series of the corresponding beta-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol. (C) 2007 Elsevier Ltd. All rights reserved.",

keywords = "SOLID-PHASE SYNTHESIS, ENANTIOSELECTIVE SYNTHESIS, ASYMMETRIC-SYNTHESIS, ORGANIC-SYNTHESIS, SMALL MOLECULES, ALDOL REACTIONS, IRON COMPLEXES, LITHIUM AMIDES, DERIVATIVES, LIBRARY",

author = "Davies, {Stephen G.} and Mulvaney, {Andrew W.} and Russell, {Angela J.} and Smith, {Andrew D.}",

year = "2007",

month = jul,

day = "17",

doi = "10.1016/j.tetasy.2007.06.008",

language = "English",

volume = "18",

pages = "1554--1566",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "13",

}

TY - JOUR

T1 - Parallel synthesis of homochiral beta-amino acids

AU - Davies, Stephen G.

AU - Mulvaney, Andrew W.

AU - Russell, Angela J.

AU - Smith, Andrew D.

PY - 2007/7/17

Y1 - 2007/7/17

N2 - The parallel asymmetric synthesis of an array of 30 P-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 alpha,beta-unsaturated esters to both enantiomeric series of the corresponding beta-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol. (C) 2007 Elsevier Ltd. All rights reserved.

AB - The parallel asymmetric synthesis of an array of 30 P-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 alpha,beta-unsaturated esters to both enantiomeric series of the corresponding beta-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol. (C) 2007 Elsevier Ltd. All rights reserved.

KW - SOLID-PHASE SYNTHESIS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - ASYMMETRIC-SYNTHESIS

KW - ORGANIC-SYNTHESIS

KW - SMALL MOLECULES

KW - ALDOL REACTIONS

KW - IRON COMPLEXES

KW - LITHIUM AMIDES

KW - DERIVATIVES

KW - LIBRARY

U2 - 10.1016/j.tetasy.2007.06.008

DO - 10.1016/j.tetasy.2007.06.008

M3 - Article

SN - 0957-4166

VL - 18

SP - 1554

EP - 1566

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 13

ER -

Parallel synthesis of homochiral beta-amino acids

Abstract

Keywords

Access to Document

Fingerprint

Cite this