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Access to All‐Carbon Spirocycles through a Carbene and Thiourea Cocatalytic Desymmetrization Cascade Reaction
Author(s) -
Zhuo Shitian,
Zhu Tingshun,
Zhou Liejin,
Mou Chengli,
Chai Huifang,
Lu Yunpeng,
Pan Lutai,
Jin Zhichao,
Chi Yonggui Robin
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810638
Subject(s) - carbene , thiourea , desymmetrization , enantioselective synthesis , organocatalysis , chemistry , combinatorial chemistry , catalysis , organic chemistry
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.