Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester

Shaojin Chen; Lin Hao; Yuexia Zhang; Bhoopendra Tiwari; Yonggui Robin Chi

doi:10.1021/ol402877n

Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester

Shaojin Chen, Lin Hao, Yuexia Zhang, Bhoopendra Tiwari, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

80 Citations (Scopus)

Abstract

An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α,β-unsaturated imines to give α-unsubstituted δ-lactones and lactams, respectively.

Original language	English
Pages (from-to)	5822-5825
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	22
DOIs	https://doi.org/10.1021/ol402877n
Publication status	Published - Nov 15 2013
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol402877n

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title = "Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester",

abstract = "An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α,β-unsaturated imines to give α-unsubstituted δ-lactones and lactams, respectively.",

author = "Shaojin Chen and Lin Hao and Yuexia Zhang and Bhoopendra Tiwari and Chi, {Yonggui Robin}",

year = "2013",

month = nov,

day = "15",

doi = "10.1021/ol402877n",

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journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester

AU - Chen, Shaojin

AU - Hao, Lin

AU - Zhang, Yuexia

AU - Tiwari, Bhoopendra

AU - Chi, Yonggui Robin

PY - 2013/11/15

Y1 - 2013/11/15

N2 - An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α,β-unsaturated imines to give α-unsubstituted δ-lactones and lactams, respectively.

AB - An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α,β-unsaturated imines to give α-unsubstituted δ-lactones and lactams, respectively.

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U2 - 10.1021/ol402877n

DO - 10.1021/ol402877n

M3 - Article

C2 - 24160260

AN - SCOPUS:84887867010

SN - 1523-7060

VL - 15

SP - 5822

EP - 5825

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester

Abstract

ASJC Scopus Subject Areas

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