SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

Steven D. Bull; Stephen G. Davies; A. Christopher Garner; Dennis Kruchinin; Min-Suk Key; Paul M. Roberts; Edward D. Savory; Andrew D. Smith; James E. Thomson

doi:10.1039/b605244d

SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

Steven D. Bull, Stephen G. Davies, A. Christopher Garner, Dennis Kruchinin, Min-Suk Key, Paul M. Roberts, Edward D. Savory, Andrew D. Smith, James E. Thomson

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

Abstract

The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.

Original language	English
Pages (from-to)	2945-2964
Number of pages	20
Journal	Organic & Biomolecular Chemistry
Volume	4
Issue number	15
DOIs	https://doi.org/10.1039/b605244d
Publication status	Published - 7 Aug 2006

Keywords

CARBOXYLIC-ACID DERIVATIVES
ASYMMETRIC-SYNTHESIS
CHIRAL AUXILIARIES
ENANTIOSELECTIVE SYNTHESIS
KINETIC RESOLUTION
4-ISOPROPYL-5,5-DIPHENYLOXAZOLIDIN-2-ONE DIOZ
SECONDARY ALCOHOLS
ACYLATING AGENTS
AMINO-ACIDS
N-ACYLATION

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title = "SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one",

abstract = "The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.",

keywords = "CARBOXYLIC-ACID DERIVATIVES, ASYMMETRIC-SYNTHESIS, CHIRAL AUXILIARIES, ENANTIOSELECTIVE SYNTHESIS, KINETIC RESOLUTION, 4-ISOPROPYL-5,5-DIPHENYLOXAZOLIDIN-2-ONE DIOZ, SECONDARY ALCOHOLS, ACYLATING AGENTS, AMINO-ACIDS, N-ACYLATION",

author = "Bull, {Steven D.} and Davies, {Stephen G.} and Garner, {A. Christopher} and Dennis Kruchinin and Min-Suk Key and Roberts, {Paul M.} and Savory, {Edward D.} and Smith, {Andrew D.} and Thomson, {James E.}",

year = "2006",

month = aug,

day = "7",

doi = "10.1039/b605244d",

language = "English",

volume = "4",

pages = "2945--2964",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0539",

publisher = "Royal Society of Chemistry",

number = "15",

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TY - JOUR

T1 - SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

AU - Bull, Steven D.

AU - Davies, Stephen G.

AU - Garner, A. Christopher

AU - Kruchinin, Dennis

AU - Key, Min-Suk

AU - Roberts, Paul M.

AU - Savory, Edward D.

AU - Smith, Andrew D.

AU - Thomson, James E.

PY - 2006/8/7

Y1 - 2006/8/7

N2 - The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.

AB - The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.

KW - CARBOXYLIC-ACID DERIVATIVES

KW - ASYMMETRIC-SYNTHESIS

KW - CHIRAL AUXILIARIES

KW - ENANTIOSELECTIVE SYNTHESIS

KW - KINETIC RESOLUTION

KW - 4-ISOPROPYL-5,5-DIPHENYLOXAZOLIDIN-2-ONE DIOZ

KW - SECONDARY ALCOHOLS

KW - ACYLATING AGENTS

KW - AMINO-ACIDS

KW - N-ACYLATION

UR - http://www.scopus.com/inward/record.url?scp=33746191442&partnerID=8YFLogxK

U2 - 10.1039/b605244d

DO - 10.1039/b605244d

M3 - Article

SN - 1477-0539

VL - 4

SP - 2945

EP - 2964

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 15

ER -

SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

Abstract

Keywords

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