Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries

Jing Lin; Wing Hong CHAN; Albert W M LEE; Wai Yeung WONG

doi:10.1016/S0040-4020(99)00872-8

Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries

Jing Lin, Wing Hong CHAN^*, Albert W M LEE, Wai Yeung WONG

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

32 Citations (Scopus)

Abstract

The use of enantiomerically pure sultams (+)-1 and (-)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic α- bromopropanoate or α-bromobutanoate, the enolates of the corresponding N- acyl sultam underwent highly diastereoselective alkylations to afford products with a complete absolute control of two contiguous chiral centres.

Original language	English
Pages (from-to)	13983-13998
Number of pages	16
Journal	Tetrahedron
Volume	55
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4020(99)00872-8
Publication status	Published - 3 Dec 1999

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

User-Defined Keywords

Asymmetric alkylation
Chiral suitams
Kinetic resolution

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10.1016/S0040-4020(99)00872-8

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title = "Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries",

abstract = "The use of enantiomerically pure sultams (+)-1 and (-)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic α- bromopropanoate or α-bromobutanoate, the enolates of the corresponding N- acyl sultam underwent highly diastereoselective alkylations to afford products with a complete absolute control of two contiguous chiral centres.",

keywords = "Asymmetric alkylation, Chiral suitams, Kinetic resolution",

author = "Jing Lin and CHAN, {Wing Hong} and LEE, {Albert W M} and WONG, {Wai Yeung}",

note = "Funding Information: Financial support from the Faculty Research Committee of the Hong Kong Baptist University",

year = "1999",

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doi = "10.1016/S0040-4020(99)00872-8",

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TY - JOUR

T1 - Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries

AU - Lin, Jing

AU - CHAN, Wing Hong

AU - LEE, Albert W M

AU - WONG, Wai Yeung

N1 - Funding Information: Financial support from the Faculty Research Committee of the Hong Kong Baptist University

PY - 1999/12/3

Y1 - 1999/12/3

N2 - The use of enantiomerically pure sultams (+)-1 and (-)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic α- bromopropanoate or α-bromobutanoate, the enolates of the corresponding N- acyl sultam underwent highly diastereoselective alkylations to afford products with a complete absolute control of two contiguous chiral centres.

AB - The use of enantiomerically pure sultams (+)-1 and (-)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic α- bromopropanoate or α-bromobutanoate, the enolates of the corresponding N- acyl sultam underwent highly diastereoselective alkylations to afford products with a complete absolute control of two contiguous chiral centres.

KW - Asymmetric alkylation

KW - Chiral suitams

KW - Kinetic resolution

UR - http://www.scopus.com/inward/record.url?scp=0033521122&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(99)00872-8

DO - 10.1016/S0040-4020(99)00872-8

M3 - Journal article

AN - SCOPUS:0033521122

SN - 0040-4020

VL - 55

SP - 13983

EP - 13998

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries

Abstract

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