Asymmetric Phosphine-Catalyzed [4+1] Annulations of o-Quinone Methides with MBH Carbonates

Tao Zhou; Tong Xia; Zhenli Liu; Lu Liu; Junliang Zhang

doi:10.1002/adsc.201801152

Asymmetric Phosphine-Catalyzed [4+1] Annulations of o-Quinone Methides with MBH Carbonates

Tao Zhou, Tong Xia, Zhenli Liu, Lu Liu, Junliang Zhang

School of Chemistry and Molecular Engineering

East China Normal University

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

63 Scopus citations

Abstract

Chiral dihydrobenzofuran units are frequently present in molecules with significant biological and pharmaceutical activities. Herein, we present the first enantioselective formal [4+1] annulation of Morita-Baylis-Hillman carbonates with o-quinone methides (o-QMs) catalyzed by a newly designed chiral phosphine catalyst. Under the mild and eco-friendly conditions, a wide range of polysubstituted dihydrobenzofurans were obtained in good yields with excellent enantioselectivities. (Figure presented.).

Original language	English
Pages (from-to)	4475-4479
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	23
DOIs	https://doi.org/10.1002/adsc.201801152
State	Published - 3 Dec 2018

Keywords

MBH carbonates
[4+1] Annulation
asymmetric catalysis
chiral phosphines
ortho-quinone methides

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10.1002/adsc.201801152

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title = "Asymmetric Phosphine-Catalyzed [4+1] Annulations of o-Quinone Methides with MBH Carbonates",

abstract = "Chiral dihydrobenzofuran units are frequently present in molecules with significant biological and pharmaceutical activities. Herein, we present the first enantioselective formal [4+1] annulation of Morita-Baylis-Hillman carbonates with o-quinone methides (o-QMs) catalyzed by a newly designed chiral phosphine catalyst. Under the mild and eco-friendly conditions, a wide range of polysubstituted dihydrobenzofurans were obtained in good yields with excellent enantioselectivities. (Figure presented.).",

keywords = "MBH carbonates, [4+1] Annulation, asymmetric catalysis, chiral phosphines, ortho-quinone methides",

author = "Tao Zhou and Tong Xia and Zhenli Liu and Lu Liu and Junliang Zhang",

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T1 - Asymmetric Phosphine-Catalyzed [4+1] Annulations of o-Quinone Methides with MBH Carbonates

AU - Zhou, Tao

AU - Xia, Tong

AU - Liu, Zhenli

AU - Liu, Lu

AU - Zhang, Junliang

PY - 2018/12/3

Y1 - 2018/12/3

N2 - Chiral dihydrobenzofuran units are frequently present in molecules with significant biological and pharmaceutical activities. Herein, we present the first enantioselective formal [4+1] annulation of Morita-Baylis-Hillman carbonates with o-quinone methides (o-QMs) catalyzed by a newly designed chiral phosphine catalyst. Under the mild and eco-friendly conditions, a wide range of polysubstituted dihydrobenzofurans were obtained in good yields with excellent enantioselectivities. (Figure presented.).

AB - Chiral dihydrobenzofuran units are frequently present in molecules with significant biological and pharmaceutical activities. Herein, we present the first enantioselective formal [4+1] annulation of Morita-Baylis-Hillman carbonates with o-quinone methides (o-QMs) catalyzed by a newly designed chiral phosphine catalyst. Under the mild and eco-friendly conditions, a wide range of polysubstituted dihydrobenzofurans were obtained in good yields with excellent enantioselectivities. (Figure presented.).

KW - MBH carbonates

KW - [4+1] Annulation

KW - asymmetric catalysis

KW - chiral phosphines

KW - ortho-quinone methides

UR - https://www.scopus.com/pages/publications/85055353989

U2 - 10.1002/adsc.201801152

DO - 10.1002/adsc.201801152

M3 - 文章

AN - SCOPUS:85055353989

SN - 1615-4150

VL - 360

SP - 4475

EP - 4479

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 23

ER -

Asymmetric Phosphine-Catalyzed [4+1] Annulations of o-Quinone Methides with MBH Carbonates

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Keywords

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