One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters

Yun Lin Liu; Xin Wang; Yu Lei Zhao; Feng Zhu; Xing Ping Zeng; Long Chen; Cui Hong Wang; Xiao Li Zhao; Jian Zhou

doi:10.1002/anie.201307250

One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters

Yun Lin Liu
, Xin Wang
, Yu Lei Zhao
, Feng Zhu
, Xing Ping Zeng
, Long Chen
, Cui Hong Wang
, Xiao Li Zhao
, Jian Zhou

School of Chemistry and Molecular Engineering

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

220 Scopus citations

Abstract

All in a sequence: An organocatalyzed Morita-Baylis-Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins.

Original language	English
Pages (from-to)	13735-13739
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	51
DOIs	https://doi.org/10.1002/anie.201307250
State	Published - 16 Dec 2013

Keywords

asymmetric catalysis
heterocycles
organocatalysis
spiro compounds
synthetic methods

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10.1002/anie.201307250

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title = "One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters",

abstract = "All in a sequence: An organocatalyzed Morita-Baylis-Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins.",

keywords = "asymmetric catalysis, heterocycles, organocatalysis, spiro compounds, synthetic methods",

author = "Liu, \{Yun Lin\} and Xin Wang and Zhao, \{Yu Lei\} and Feng Zhu and Zeng, \{Xing Ping\} and Long Chen and Wang, \{Cui Hong\} and Zhao, \{Xiao Li\} and Jian Zhou",

year = "2013",

month = dec,

day = "16",

doi = "10.1002/anie.201307250",

language = "英语",

volume = "52",

pages = "13735--13739",

journal = "Angewandte Chemie - International Edition",

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T1 - One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters

AU - Liu, Yun Lin

AU - Wang, Xin

AU - Zhao, Yu Lei

AU - Zhu, Feng

AU - Zeng, Xing Ping

AU - Chen, Long

AU - Wang, Cui Hong

AU - Zhao, Xiao Li

AU - Zhou, Jian

PY - 2013/12/16

Y1 - 2013/12/16

N2 - All in a sequence: An organocatalyzed Morita-Baylis-Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins.

AB - All in a sequence: An organocatalyzed Morita-Baylis-Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins.

KW - asymmetric catalysis

KW - heterocycles

KW - organocatalysis

KW - spiro compounds

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/84890480675

U2 - 10.1002/anie.201307250

DO - 10.1002/anie.201307250

M3 - 文章

C2 - 24346948

AN - SCOPUS:84890480675

SN - 1433-7851

VL - 52

SP - 13735

EP - 13739

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 51

ER -

One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters

Abstract

Keywords

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