A general asymmetric route to enantio-enriched isoflavanes via an organocatalytic annulation of o-quinone methides and aldehydes

Jian Zhang; Shuangzhan Zhang; Huixin Yang; Ding Zhou; Xueting Yu; Wei Wang; Hexin Xie

doi:10.1016/j.tetlet.2018.05.016

A general asymmetric route to enantio-enriched isoflavanes via an organocatalytic annulation of o-quinone methides and aldehydes

Jian Zhang
, Shuangzhan Zhang
, Huixin Yang
, Ding Zhou
, Xueting Yu
, Wei Wang
, Hexin Xie

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

10 Scopus citations

Abstract

Reported herein is a general approach to optically active isoflavanes based on a chiral amine-catalyzed [4 + 2] asymmetric annulation of o-quinone methides and aldehydes. A number of naturally occurring isoflavanes, including equol, sativan, isosativan, vestitol and medicarpin, as well as isoflavane analogues were readily prepared with good to excellent enantioselectivities.

Original language	English (US)
Pages (from-to)	2407-2411
Number of pages	5
Journal	Tetrahedron Letters
Volume	59
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2018.05.016
State	Published - Jun 20 2018
Externally published	Yes

Keywords

Asymmetric
Isoflavanes
Organocatalysis
o-Quinone methide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2018.05.016

Cite this

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title = "A general asymmetric route to enantio-enriched isoflavanes via an organocatalytic annulation of o-quinone methides and aldehydes",

abstract = "Reported herein is a general approach to optically active isoflavanes based on a chiral amine-catalyzed [4 + 2] asymmetric annulation of o-quinone methides and aldehydes. A number of naturally occurring isoflavanes, including equol, sativan, isosativan, vestitol and medicarpin, as well as isoflavane analogues were readily prepared with good to excellent enantioselectivities.",

keywords = "Asymmetric, Isoflavanes, Organocatalysis, o-Quinone methide",

author = "Jian Zhang and Shuangzhan Zhang and Huixin Yang and Ding Zhou and Xueting Yu and Wei Wang and Hexin Xie",

note = "Funding Information: We thank the National Natural Science Foundation of China ( 21472048 ), the “Thousand Plan” Youth Program, and the Fundamental Research Funds for the Central Universities for financial support. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

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T1 - A general asymmetric route to enantio-enriched isoflavanes via an organocatalytic annulation of o-quinone methides and aldehydes

AU - Zhang, Jian

AU - Zhang, Shuangzhan

AU - Yang, Huixin

AU - Zhou, Ding

AU - Yu, Xueting

AU - Wang, Wei

AU - Xie, Hexin

N1 - Funding Information: We thank the National Natural Science Foundation of China ( 21472048 ), the “Thousand Plan” Youth Program, and the Fundamental Research Funds for the Central Universities for financial support. Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/6/20

Y1 - 2018/6/20

N2 - Reported herein is a general approach to optically active isoflavanes based on a chiral amine-catalyzed [4 + 2] asymmetric annulation of o-quinone methides and aldehydes. A number of naturally occurring isoflavanes, including equol, sativan, isosativan, vestitol and medicarpin, as well as isoflavane analogues were readily prepared with good to excellent enantioselectivities.

AB - Reported herein is a general approach to optically active isoflavanes based on a chiral amine-catalyzed [4 + 2] asymmetric annulation of o-quinone methides and aldehydes. A number of naturally occurring isoflavanes, including equol, sativan, isosativan, vestitol and medicarpin, as well as isoflavane analogues were readily prepared with good to excellent enantioselectivities.

KW - Asymmetric

KW - Isoflavanes

KW - Organocatalysis

KW - o-Quinone methide

UR - https://www.scopus.com/pages/publications/85047098027

UR - https://www.scopus.com/pages/publications/85047098027#tab=citedBy

U2 - 10.1016/j.tetlet.2018.05.016

DO - 10.1016/j.tetlet.2018.05.016

M3 - Article

AN - SCOPUS:85047098027

SN - 0040-4039

VL - 59

SP - 2407

EP - 2411

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

A general asymmetric route to enantio-enriched isoflavanes via an organocatalytic annulation of o-quinone methides and aldehydes

Abstract

Keywords

ASJC Scopus subject areas

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