Organocatalytic Asymmetric Michael/Cyclization Cascade Reaction of 3-Isothiocyanato Oxindoles with Maleimides for the Efficient Construction of Pyrrolidonyl Spirooxindoles

Lei Liu; Bo Liang Zhao; Da Ming Du

doi:10.1002/ejoc.201600658

Organocatalytic Asymmetric Michael/Cyclization Cascade Reaction of 3-Isothiocyanato Oxindoles with Maleimides for the Efficient Construction of Pyrrolidonyl Spirooxindoles

Lei Liu
, Bo Liang Zhao
, Da Ming Du^*

^*Corresponding author for this work

Beijing Institute of Technology

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

32 Citations (Scopus)

Abstract

The development of a Michael/cyclization cascade reaction between 3-isothiocyanato-oxindoles and maleimide catalyzed by chrial squaramides is reported. This protocol provides a series of pyrrolidonyl spirooxindoles bearing three contiguous stereocenters in excellent yields (up to 99 %) with high diastereo- and enantioselectivities (up to >99:1 dr, 91 % ee).

Original language	English
Pages (from-to)	4711-4718
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	27
DOIs	https://doi.org/10.1002/ejoc.201600658
Publication status	Published - Sept 2016

Keywords

Asymmetric catalysis
Cascade reactions
Cyclization
Michael addition
Nitrogen heterocycles
Spiro compounds

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10.1002/ejoc.201600658

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title = "Organocatalytic Asymmetric Michael/Cyclization Cascade Reaction of 3-Isothiocyanato Oxindoles with Maleimides for the Efficient Construction of Pyrrolidonyl Spirooxindoles",

abstract = "The development of a Michael/cyclization cascade reaction between 3-isothiocyanato-oxindoles and maleimide catalyzed by chrial squaramides is reported. This protocol provides a series of pyrrolidonyl spirooxindoles bearing three contiguous stereocenters in excellent yields (up to 99 \%) with high diastereo- and enantioselectivities (up to >99:1 dr, 91 \% ee).",

keywords = "Asymmetric catalysis, Cascade reactions, Cyclization, Michael addition, Nitrogen heterocycles, Spiro compounds",

author = "Lei Liu and Zhao, \{Bo Liang\} and Du, \{Da Ming\}",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2016",

month = sep,

doi = "10.1002/ejoc.201600658",

language = "English",

volume = "2016",

pages = "4711--4718",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH Verlag",

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T1 - Organocatalytic Asymmetric Michael/Cyclization Cascade Reaction of 3-Isothiocyanato Oxindoles with Maleimides for the Efficient Construction of Pyrrolidonyl Spirooxindoles

AU - Liu, Lei

AU - Zhao, Bo Liang

AU - Du, Da Ming

PY - 2016/9

Y1 - 2016/9

N2 - The development of a Michael/cyclization cascade reaction between 3-isothiocyanato-oxindoles and maleimide catalyzed by chrial squaramides is reported. This protocol provides a series of pyrrolidonyl spirooxindoles bearing three contiguous stereocenters in excellent yields (up to 99 %) with high diastereo- and enantioselectivities (up to >99:1 dr, 91 % ee).

AB - The development of a Michael/cyclization cascade reaction between 3-isothiocyanato-oxindoles and maleimide catalyzed by chrial squaramides is reported. This protocol provides a series of pyrrolidonyl spirooxindoles bearing three contiguous stereocenters in excellent yields (up to 99 %) with high diastereo- and enantioselectivities (up to >99:1 dr, 91 % ee).

KW - Asymmetric catalysis

KW - Cascade reactions

KW - Cyclization

KW - Michael addition

KW - Nitrogen heterocycles

KW - Spiro compounds

UR - https://www.scopus.com/pages/publications/84983678523

U2 - 10.1002/ejoc.201600658

DO - 10.1002/ejoc.201600658

M3 - Article

AN - SCOPUS:84983678523

SN - 1434-193X

VL - 2016

SP - 4711

EP - 4718

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 27

ER -

Organocatalytic Asymmetric Michael/Cyclization Cascade Reaction of 3-Isothiocyanato Oxindoles with Maleimides for the Efficient Construction of Pyrrolidonyl Spirooxindoles

Abstract

Keywords

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