Access to All-Carbon Spirocycles through a Carbene and Thiourea Cocatalytic Desymmetrization Cascade Reaction

Shitian Zhuo; Tingshun Zhu; Liejin Zhou; Chengli Mou; Huifang Chai; Yunpeng Lu; Lutai Pan; Zhichao Jin; Yonggui Robin Chi

doi:10.1002/anie.201810638

Access to All-Carbon Spirocycles through a Carbene and Thiourea Cocatalytic Desymmetrization Cascade Reaction

Shitian Zhuo, Tingshun Zhu, Liejin Zhou, Chengli Mou, Huifang Chai, Yunpeng Lu, Lutai Pan^*, Zhichao Jin, Yonggui Robin Chi

^*Corresponding author for this work

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

57 Citations (Scopus)

Abstract

A new catalytic approach for rapid asymmetric access to spirocycles is disclosed. The reaction involves a carbene- and thiourea-cocatalyzed desymmetrization process with the simultaneous installation of a spirocyclic core. The use of a thiourea cocatalyst is critical to turn on this reaction, as no product was formed in the absence of a thiourea. Our study constitutes the first success in the carbene-catalyzed enantioselective synthesis of all-carbon spirocycles. The reaction products can be readily transformed into sophisticated multicyclic molecules and chiral ligands.

Original language	English
Pages (from-to)	1784-1788
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	6
DOIs	https://doi.org/10.1002/anie.201810638
Publication status	Published - Feb 4 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

desymmetrization
dual catalysis
N-heterocyclic carbenes
quaternary stereocenters
spiro compounds

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10.1002/anie.201810638

Cite this

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title = "Access to All-Carbon Spirocycles through a Carbene and Thiourea Cocatalytic Desymmetrization Cascade Reaction",

abstract = "A new catalytic approach for rapid asymmetric access to spirocycles is disclosed. The reaction involves a carbene- and thiourea-cocatalyzed desymmetrization process with the simultaneous installation of a spirocyclic core. The use of a thiourea cocatalyst is critical to turn on this reaction, as no product was formed in the absence of a thiourea. Our study constitutes the first success in the carbene-catalyzed enantioselective synthesis of all-carbon spirocycles. The reaction products can be readily transformed into sophisticated multicyclic molecules and chiral ligands.",

keywords = "desymmetrization, dual catalysis, N-heterocyclic carbenes, quaternary stereocenters, spiro compounds",

author = "Shitian Zhuo and Tingshun Zhu and Liejin Zhou and Chengli Mou and Huifang Chai and Yunpeng Lu and Lutai Pan and Zhichao Jin and Chi, {Yonggui Robin}",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

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doi = "10.1002/anie.201810638",

language = "English",

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TY - JOUR

T1 - Access to All-Carbon Spirocycles through a Carbene and Thiourea Cocatalytic Desymmetrization Cascade Reaction

AU - Zhuo, Shitian

AU - Zhu, Tingshun

AU - Zhou, Liejin

AU - Mou, Chengli

AU - Chai, Huifang

AU - Lu, Yunpeng

AU - Pan, Lutai

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2019/2/4

Y1 - 2019/2/4

N2 - A new catalytic approach for rapid asymmetric access to spirocycles is disclosed. The reaction involves a carbene- and thiourea-cocatalyzed desymmetrization process with the simultaneous installation of a spirocyclic core. The use of a thiourea cocatalyst is critical to turn on this reaction, as no product was formed in the absence of a thiourea. Our study constitutes the first success in the carbene-catalyzed enantioselective synthesis of all-carbon spirocycles. The reaction products can be readily transformed into sophisticated multicyclic molecules and chiral ligands.

AB - A new catalytic approach for rapid asymmetric access to spirocycles is disclosed. The reaction involves a carbene- and thiourea-cocatalyzed desymmetrization process with the simultaneous installation of a spirocyclic core. The use of a thiourea cocatalyst is critical to turn on this reaction, as no product was formed in the absence of a thiourea. Our study constitutes the first success in the carbene-catalyzed enantioselective synthesis of all-carbon spirocycles. The reaction products can be readily transformed into sophisticated multicyclic molecules and chiral ligands.

KW - desymmetrization

KW - dual catalysis

KW - N-heterocyclic carbenes

KW - quaternary stereocenters

KW - spiro compounds

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DO - 10.1002/anie.201810638

M3 - Article

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AN - SCOPUS:85059734938

SN - 1433-7851

VL - 58

SP - 1784

EP - 1788

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

Access to All-Carbon Spirocycles through a Carbene and Thiourea Cocatalytic Desymmetrization Cascade Reaction

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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