Evaluating beta-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction

Stephen G. Davies; Angela J. Russell; Ruth L. Sheppard; Andrew D. Smith; James E. Thomson

doi:10.1039/b711171a

Evaluating beta-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction

Stephen G. Davies, Angela J. Russell, Ruth L. Sheppard, Andrew D. Smith, James E. Thomson

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

Abstract

A systematic study of the effect of substitution within the beta-amino acid framework indicates that both beta(2)- and beta(3)-amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained beta-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.

Original language	English
Pages (from-to)	3190-3200
Number of pages	11
Journal	Organic & Biomolecular Chemistry
Volume	5
Issue number	19
DOIs	https://doi.org/10.1039/b711171a
Publication status	Published - 2007

Keywords

INTERMOLECULAR ALDOL REACTIONS
MICHAEL ADDITION-REACTIONS
ASYMMETRIC-SYNTHESIS
ALPHA,BETA-UNSATURATED ALDEHYDES
NUCLEOPHILIC CARBENES
GAMMA-BUTYROLACTONES
PROLINE DERIVATIVES
KINETIC RESOLUTION
LITHIUM AMIDES
NITRO-OLEFINS

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title = "Evaluating beta-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction",

abstract = "A systematic study of the effect of substitution within the beta-amino acid framework indicates that both beta(2)- and beta(3)-amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained beta-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.",

keywords = "INTERMOLECULAR ALDOL REACTIONS, MICHAEL ADDITION-REACTIONS, ASYMMETRIC-SYNTHESIS, ALPHA,BETA-UNSATURATED ALDEHYDES, NUCLEOPHILIC CARBENES, GAMMA-BUTYROLACTONES, PROLINE DERIVATIVES, KINETIC RESOLUTION, LITHIUM AMIDES, NITRO-OLEFINS",

author = "Davies, {Stephen G.} and Russell, {Angela J.} and Sheppard, {Ruth L.} and Smith, {Andrew D.} and Thomson, {James E.}",

year = "2007",

doi = "10.1039/b711171a",

language = "English",

volume = "5",

pages = "3190--3200",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0539",

publisher = "Royal Society of Chemistry",

number = "19",

}

TY - JOUR

T1 - Evaluating beta-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction

AU - Davies, Stephen G.

AU - Russell, Angela J.

AU - Sheppard, Ruth L.

AU - Smith, Andrew D.

AU - Thomson, James E.

PY - 2007

Y1 - 2007

N2 - A systematic study of the effect of substitution within the beta-amino acid framework indicates that both beta(2)- and beta(3)-amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained beta-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.

AB - A systematic study of the effect of substitution within the beta-amino acid framework indicates that both beta(2)- and beta(3)-amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained beta-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.

KW - INTERMOLECULAR ALDOL REACTIONS

KW - MICHAEL ADDITION-REACTIONS

KW - ASYMMETRIC-SYNTHESIS

KW - ALPHA,BETA-UNSATURATED ALDEHYDES

KW - NUCLEOPHILIC CARBENES

KW - GAMMA-BUTYROLACTONES

KW - PROLINE DERIVATIVES

KW - KINETIC RESOLUTION

KW - LITHIUM AMIDES

KW - NITRO-OLEFINS

U2 - 10.1039/b711171a

DO - 10.1039/b711171a

M3 - Article

SN - 1477-0539

VL - 5

SP - 3190

EP - 3200

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 19

ER -

Evaluating beta-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction

Abstract

Keywords

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