Access to all-carbon spirocycles through a carbene and thiourea cocatalytic desymmetrization cascade reaction

Access to all-carbon spirocycles through a carbene and thiourea cocatalytic desymmetrization cascade reaction

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...

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Bibliographic Details
Main Authors: Zhuo, Shitian, Zhu, Tingshun, Zhou, Liejin, Mou, Chengli, Chai, Huifang, Lu, Yunpeng, Pan, Lutai, Jin, Zhichao, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry::Organic chemistry
Desymmetrization
Dual Catalysis
Online Access:https://hdl.handle.net/10356/137748
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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