Organocatalytic enantioselective γ-aminoalkylation of unsaturated ester: Access to pipecolic acid derivatives

Jianfeng Xu; Zhichao Jin; Yonggui Robin Chi

doi:10.1021/ol402358k

Organocatalytic enantioselective γ-aminoalkylation of unsaturated ester: Access to pipecolic acid derivatives

Jianfeng Xu, Zhichao Jin, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

144 Citations (Scopus)

Abstract

The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.

Original language	English
Pages (from-to)	5028-5031
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	19
DOIs	https://doi.org/10.1021/ol402358k
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/ol402358k

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title = "Organocatalytic enantioselective γ-aminoalkylation of unsaturated ester: Access to pipecolic acid derivatives",

abstract = "The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.",

author = "Jianfeng Xu and Zhichao Jin and Chi, {Yonggui Robin}",

year = "2013",

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AU - Xu, Jianfeng

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2013/10/4

Y1 - 2013/10/4

N2 - The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.

AB - The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.

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Organocatalytic enantioselective γ-aminoalkylation of unsaturated ester: Access to pipecolic acid derivatives

Abstract

ASJC Scopus Subject Areas

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