Organocatalytic activation of alkylacetic esters as enolate precursors to react with α,β-unsaturated imines

Lin Hao; Shaojin Chen; Jianfeng Xu; Bhoopendra Tiwari; Zhenqian Fu; Tong Li; Jieyan Lim; Yonggui Robin Chi

doi:10.1021/ol4021805

Organocatalytic activation of alkylacetic esters as enolate precursors to react with α,β-unsaturated imines

Lin Hao, Shaojin Chen, Jianfeng Xu, Bhoopendra Tiwari, Zhenqian Fu, Tong Li, Jieyan Lim, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

87 Citations (Scopus)

Abstract

Asymmetric functionalization of alkylacetic esters and their derivatives is traditionally achieved via preformed enolates with chiral auxiliaries. Catalytic versions of such transformations are attractive but challenging. A direct catalytic activation of simple alkylacetic esters via N-heterocyclic carbene organocatalysts to generate chiral enolate intermediates for highly enantioselective reactions is reported.

Original language	English
Pages (from-to)	4956-4959
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	19
DOIs	https://doi.org/10.1021/ol4021805
Publication status	Published - Oct 4 2013
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol4021805

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abstract = "Asymmetric functionalization of alkylacetic esters and their derivatives is traditionally achieved via preformed enolates with chiral auxiliaries. Catalytic versions of such transformations are attractive but challenging. A direct catalytic activation of simple alkylacetic esters via N-heterocyclic carbene organocatalysts to generate chiral enolate intermediates for highly enantioselective reactions is reported.",

author = "Lin Hao and Shaojin Chen and Jianfeng Xu and Bhoopendra Tiwari and Zhenqian Fu and Tong Li and Jieyan Lim and Chi, {Yonggui Robin}",

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T1 - Organocatalytic activation of alkylacetic esters as enolate precursors to react with α,β-unsaturated imines

AU - Hao, Lin

AU - Chen, Shaojin

AU - Xu, Jianfeng

AU - Tiwari, Bhoopendra

AU - Fu, Zhenqian

AU - Li, Tong

AU - Lim, Jieyan

AU - Chi, Yonggui Robin

PY - 2013/10/4

Y1 - 2013/10/4

N2 - Asymmetric functionalization of alkylacetic esters and their derivatives is traditionally achieved via preformed enolates with chiral auxiliaries. Catalytic versions of such transformations are attractive but challenging. A direct catalytic activation of simple alkylacetic esters via N-heterocyclic carbene organocatalysts to generate chiral enolate intermediates for highly enantioselective reactions is reported.

AB - Asymmetric functionalization of alkylacetic esters and their derivatives is traditionally achieved via preformed enolates with chiral auxiliaries. Catalytic versions of such transformations are attractive but challenging. A direct catalytic activation of simple alkylacetic esters via N-heterocyclic carbene organocatalysts to generate chiral enolate intermediates for highly enantioselective reactions is reported.

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IS - 19

ER -

Organocatalytic activation of alkylacetic esters as enolate precursors to react with α,β-unsaturated imines

Abstract

ASJC Scopus Subject Areas

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