Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s

Xiaofeng Zhang; Weiqi Qiu; Stephanie A. Murray; Desheng Zhan; Jason Evans; Jerry P. Jasinski; Xiao Wang; Wei Zhang

doi:10.1021/acs.joc.1c01797

Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s

Xiaofeng Zhang
, Weiqi Qiu
, Stephanie A. Murray
, Desheng Zhan
, Jason Evans
, Jerry P. Jasinski
, Xiao Wang
, Wei Zhang

Chemistry

University of Massachusetts Boston
Dana-Farber Cancer Institute
Harvard University
Changchun Normal University
Keene State College
Nanjing University

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

Abstract

A pseudo-five-component reaction involving double decarboxylative 1,3-dipolar cycloaddition of azomethine ylides with olefinic oxindoles for the diastereoselective synthesis of bispiro[oxindole-pyrrolidine]s is developed. The major diastereomers are unique butterfly shaped compounds with a plane of symmetry. Recyclable zeolite HY acid catalyst is used to promote the reaction, and only CO2 and H2O are generated as byproducts.

Original language	English
Pages (from-to)	17395-17403
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	86
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.1c01797
State	Published - Dec 3 2021

ASJC Scopus Subject Areas

Organic Chemistry

Access to Document

10.1021/acs.joc.1c01797

Cite this

@article{db0fba376b5949bc8b78330dbfca6fc5,

title = "Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s",

abstract = "A pseudo-five-component reaction involving double decarboxylative 1,3-dipolar cycloaddition of azomethine ylides with olefinic oxindoles for the diastereoselective synthesis of bispiro[oxindole-pyrrolidine]s is developed. The major diastereomers are unique butterfly shaped compounds with a plane of symmetry. Recyclable zeolite HY acid catalyst is used to promote the reaction, and only CO2 and H2O are generated as byproducts.",

author = "Xiaofeng Zhang and Weiqi Qiu and Murray, \{Stephanie A.\} and Desheng Zhan and Jason Evans and Jasinski, \{Jerry P.\} and Xiao Wang and Wei Zhang",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = dec,

day = "3",

doi = "10.1021/acs.joc.1c01797",

language = "English",

volume = "86",

pages = "17395--17403",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s

AU - Zhang, Xiaofeng

AU - Qiu, Weiqi

AU - Murray, Stephanie A.

AU - Zhan, Desheng

AU - Evans, Jason

AU - Jasinski, Jerry P.

AU - Wang, Xiao

AU - Zhang, Wei

PY - 2021/12/3

Y1 - 2021/12/3

N2 - A pseudo-five-component reaction involving double decarboxylative 1,3-dipolar cycloaddition of azomethine ylides with olefinic oxindoles for the diastereoselective synthesis of bispiro[oxindole-pyrrolidine]s is developed. The major diastereomers are unique butterfly shaped compounds with a plane of symmetry. Recyclable zeolite HY acid catalyst is used to promote the reaction, and only CO2 and H2O are generated as byproducts.

AB - A pseudo-five-component reaction involving double decarboxylative 1,3-dipolar cycloaddition of azomethine ylides with olefinic oxindoles for the diastereoselective synthesis of bispiro[oxindole-pyrrolidine]s is developed. The major diastereomers are unique butterfly shaped compounds with a plane of symmetry. Recyclable zeolite HY acid catalyst is used to promote the reaction, and only CO2 and H2O are generated as byproducts.

UR - https://www.scopus.com/pages/publications/85120381005

UR - https://www.scopus.com/pages/publications/85120381005#tab=citedBy

U2 - 10.1021/acs.joc.1c01797

DO - 10.1021/acs.joc.1c01797

M3 - Article

AN - SCOPUS:85120381005

SN - 0022-3263

VL - 86

SP - 17395

EP - 17403

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s

Abstract

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this