Organocatalytic annulation of aldehydes and o-quinone methides: A facile access to dihydrocoumarins

Ding Zhou; Kaizhe Mao; Jian Zhang; Bingliang Yan; Wei Wang; Hexin Xie

doi:10.1016/j.tetlet.2016.11.006

Organocatalytic annulation of aldehydes and o-quinone methides: A facile access to dihydrocoumarins

Ding Zhou, Kaizhe Mao, Jian Zhang, Bingliang Yan, Wei Wang, Hexin Xie

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

18 Scopus citations

Abstract

A [4+2] annulation of aldehydes and o-quinone methides catalyzed by a secondary amine is developed. This process leads to biologically important dihydrocoumarins in moderate to good yields after oxidation. In addition, the employment of a chiral secondary amine catalyst allows access to optically active dihydrocoumarins with up to 64% ee.

Original language	English (US)
Pages (from-to)	5649-5652
Number of pages	4
Journal	Tetrahedron Letters
Volume	57
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2016.11.006
State	Published - 2016
Externally published	Yes

Keywords

Dihydrocoumarin
Organocatalysis
o-Quinone methide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2016.11.006

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title = "Organocatalytic annulation of aldehydes and o-quinone methides: A facile access to dihydrocoumarins",

abstract = "A [4+2] annulation of aldehydes and o-quinone methides catalyzed by a secondary amine is developed. This process leads to biologically important dihydrocoumarins in moderate to good yields after oxidation. In addition, the employment of a chiral secondary amine catalyst allows access to optically active dihydrocoumarins with up to 64% ee.",

keywords = "Dihydrocoumarin, Organocatalysis, o-Quinone methide",

author = "Ding Zhou and Kaizhe Mao and Jian Zhang and Bingliang Yan and Wei Wang and Hexin Xie",

note = "Funding Information: This work was financially supported by the “Thousand Plan” Youth Program, the Fundamental Research Funds for the Central Universities, and East China University of Science & Technology . Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.tetlet.2016.11.006",

language = "English (US)",

volume = "57",

pages = "5649--5652",

journal = "Tetrahedron Letters",

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number = "50",

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TY - JOUR

T1 - Organocatalytic annulation of aldehydes and o-quinone methides

T2 - A facile access to dihydrocoumarins

AU - Zhou, Ding

AU - Mao, Kaizhe

AU - Zhang, Jian

AU - Yan, Bingliang

AU - Wang, Wei

AU - Xie, Hexin

N1 - Funding Information: This work was financially supported by the “Thousand Plan” Youth Program, the Fundamental Research Funds for the Central Universities, and East China University of Science & Technology . Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - A [4+2] annulation of aldehydes and o-quinone methides catalyzed by a secondary amine is developed. This process leads to biologically important dihydrocoumarins in moderate to good yields after oxidation. In addition, the employment of a chiral secondary amine catalyst allows access to optically active dihydrocoumarins with up to 64% ee.

AB - A [4+2] annulation of aldehydes and o-quinone methides catalyzed by a secondary amine is developed. This process leads to biologically important dihydrocoumarins in moderate to good yields after oxidation. In addition, the employment of a chiral secondary amine catalyst allows access to optically active dihydrocoumarins with up to 64% ee.

KW - Dihydrocoumarin

KW - Organocatalysis

KW - o-Quinone methide

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U2 - 10.1016/j.tetlet.2016.11.006

DO - 10.1016/j.tetlet.2016.11.006

M3 - Article

AN - SCOPUS:84996593395

SN - 0040-4039

VL - 57

SP - 5649

EP - 5652

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Organocatalytic annulation of aldehydes and o-quinone methides: A facile access to dihydrocoumarins

Abstract

Keywords

ASJC Scopus subject areas

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