Highly diastereoselective multicomponent cascade reactions: Efficient synthesis of functionalized 1-indanols

Jun Jiang; Xiaoyu Guan; Shunying Liu; Baiyan Ren; Xiaochu Ma; Xin Guo; Fengping Lv; Xiang Wu; Wenhao Hu

doi:10.1002/anie.201208391

Highly diastereoselective multicomponent cascade reactions: Efficient synthesis of functionalized 1-indanols

Jun Jiang, Xiaoyu Guan, Shunying Liu, Baiyan Ren, Xiaochu Ma, Xin Guo, Fengping Lv, Xiang Wu, Wenhao Hu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

41 Scopus citations

Abstract

Trapped: A Michael-aldol-type cascade reaction including the trapping of an oxonium ylide through a delayed proton shift leads to the formation of multiple stereocenters in a mild one-pot synthesis. Enantiomerically pure indanol derivatives with four stereocenters and a stereogenic quaternary carbon center were easily obtained through this method in moderate to good yields.

Original language	English
Pages (from-to)	1539-1542
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	5
DOIs	https://doi.org/10.1002/anie.201208391
State	Published - 28 Jan 2013

Keywords

cascade reactions
diastereoselectivity
multicomponent reactions
oxonium ylides
stereogenic centers

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10.1002/anie.201208391

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title = "Highly diastereoselective multicomponent cascade reactions: Efficient synthesis of functionalized 1-indanols",

abstract = "Trapped: A Michael-aldol-type cascade reaction including the trapping of an oxonium ylide through a delayed proton shift leads to the formation of multiple stereocenters in a mild one-pot synthesis. Enantiomerically pure indanol derivatives with four stereocenters and a stereogenic quaternary carbon center were easily obtained through this method in moderate to good yields.",

keywords = "cascade reactions, diastereoselectivity, multicomponent reactions, oxonium ylides, stereogenic centers",

author = "Jun Jiang and Xiaoyu Guan and Shunying Liu and Baiyan Ren and Xiaochu Ma and Xin Guo and Fengping Lv and Xiang Wu and Wenhao Hu",

year = "2013",

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TY - JOUR

T1 - Highly diastereoselective multicomponent cascade reactions

T2 - Efficient synthesis of functionalized 1-indanols

AU - Jiang, Jun

AU - Guan, Xiaoyu

AU - Liu, Shunying

AU - Ren, Baiyan

AU - Ma, Xiaochu

AU - Guo, Xin

AU - Lv, Fengping

AU - Wu, Xiang

AU - Hu, Wenhao

PY - 2013/1/28

Y1 - 2013/1/28

N2 - Trapped: A Michael-aldol-type cascade reaction including the trapping of an oxonium ylide through a delayed proton shift leads to the formation of multiple stereocenters in a mild one-pot synthesis. Enantiomerically pure indanol derivatives with four stereocenters and a stereogenic quaternary carbon center were easily obtained through this method in moderate to good yields.

AB - Trapped: A Michael-aldol-type cascade reaction including the trapping of an oxonium ylide through a delayed proton shift leads to the formation of multiple stereocenters in a mild one-pot synthesis. Enantiomerically pure indanol derivatives with four stereocenters and a stereogenic quaternary carbon center were easily obtained through this method in moderate to good yields.

KW - cascade reactions

KW - diastereoselectivity

KW - multicomponent reactions

KW - oxonium ylides

KW - stereogenic centers

UR - https://www.scopus.com/pages/publications/84872874291

U2 - 10.1002/anie.201208391

DO - 10.1002/anie.201208391

M3 - 文章

C2 - 23280673

AN - SCOPUS:84872874291

SN - 1433-7851

VL - 52

SP - 1539

EP - 1542

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 5

ER -

Highly diastereoselective multicomponent cascade reactions: Efficient synthesis of functionalized 1-indanols

Abstract

Keywords

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