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Nickel‐Catalyzed Chemo‐ and Enantioselective Coupling between Cyclobutanones and Allenes: Rapid Synthesis of [3.2.2] Bicycles
Author(s) -
Zhou Xuan,
Dong Guangbin
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201609489
Subject(s) - intramolecular force , catalysis , nickel , enantioselective synthesis , chemistry , combinatorial chemistry , cleavage (geology) , bicyclic molecule , redox , coupling (piping) , stereochemistry , organic chemistry , materials science , metallurgy , fracture (geology) , composite material
Abstract Herein an intramolecular nickel‐catalyzed (4+2) coupling between cyclobutanones and allenes, by C−C cleavage, is reported. The reaction provides a distinct approach for accessing [3.2.2] bicyclic scaffolds which are challenging to prepare through conventional approaches. The reaction is efficient, chemoselective, and pH/redox neutral. Room temperature conditions and low catalyst loadings can be adopted. Excellent enantioselectivity is also achieved.