Asymmetric Synthesis of cis-3,4-Dihydrocoumarins via [4 + 2] Cycloadditions Catalyzed by Amidine Derivatives

Jing Hai Jin; Xiang Yu Li; Xiaoyan Luo; John S. Fossey; Wei Ping Deng

doi:10.1021/acs.joc.7b00367

Asymmetric Synthesis of cis-3,4-Dihydrocoumarins via [4 + 2] Cycloadditions Catalyzed by Amidine Derivatives

Jing Hai Jin, Xiang Yu Li, Xiaoyan Luo, John S. Fossey, Wei Ping Deng^*

^*Corresponding author for this work

Chemistry

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

31 Citations (Scopus)

Abstract

A highly efficient chiral amidine derivative-catalyzed tandem Michael addition/lactonization of carboxylic acids and o-quinone methides (o-QMs) has been developed that enables the asymmetric synthesis of cis-3,4-dihydrocoumarins bearing contiguous tertiary stereogenic centers in high yields with excellent stereoselectivities.

Original language	English
Pages (from-to)	5424-5432
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	82
Issue number	10
Early online date	25 Apr 2017
DOIs	https://doi.org/10.1021/acs.joc.7b00367
Publication status	Published - 19 May 2017

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.7b00367

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title = "Asymmetric Synthesis of cis-3,4-Dihydrocoumarins via [4 + 2] Cycloadditions Catalyzed by Amidine Derivatives",

abstract = "A highly efficient chiral amidine derivative-catalyzed tandem Michael addition/lactonization of carboxylic acids and o-quinone methides (o-QMs) has been developed that enables the asymmetric synthesis of cis-3,4-dihydrocoumarins bearing contiguous tertiary stereogenic centers in high yields with excellent stereoselectivities.",

author = "Jin, {Jing Hai} and Li, {Xiang Yu} and Xiaoyan Luo and Fossey, {John S.} and Deng, {Wei Ping}",

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AU - Jin, Jing Hai

AU - Li, Xiang Yu

AU - Luo, Xiaoyan

AU - Fossey, John S.

AU - Deng, Wei Ping

PY - 2017/5/19

Y1 - 2017/5/19

N2 - A highly efficient chiral amidine derivative-catalyzed tandem Michael addition/lactonization of carboxylic acids and o-quinone methides (o-QMs) has been developed that enables the asymmetric synthesis of cis-3,4-dihydrocoumarins bearing contiguous tertiary stereogenic centers in high yields with excellent stereoselectivities.

AB - A highly efficient chiral amidine derivative-catalyzed tandem Michael addition/lactonization of carboxylic acids and o-quinone methides (o-QMs) has been developed that enables the asymmetric synthesis of cis-3,4-dihydrocoumarins bearing contiguous tertiary stereogenic centers in high yields with excellent stereoselectivities.

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U2 - 10.1021/acs.joc.7b00367

DO - 10.1021/acs.joc.7b00367

M3 - Article

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SN - 0022-3263

VL - 82

SP - 5424

EP - 5432

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Asymmetric Synthesis of cis-3,4-Dihydrocoumarins via [4 + 2] Cycloadditions Catalyzed by Amidine Derivatives

Abstract

ASJC Scopus subject areas

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