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Hydrocyanative Cyclization and Three‐Component Cross‐Coupling Reaction between Allenes and Alkynes under Nickel Catalysis
Author(s) -
Arai Shigeru,
Amako Yuka,
Yang Xiaofei,
Nishida Atsushi
Publication year - 2013
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.201303883
Subject(s) - regioselectivity , alkyne , chemistry , stereoselectivity , catalysis , coupling reaction , acetone , nickel , medicinal chemistry , organic chemistry , combinatorial chemistry
Packed with functionality : The key step in the title reactions with acetone cyanohydrin is a regioselective hydronickelation of allenes. Subsequent carbometalation of the alkyne followed by reductive elimination gave cyano‐functionalized tetrasubstituted alkenes in a regio‐ and stereoselective manner (see scheme; EWG=electron‐withdrawing group, Ts= p ‐toluenesulfonyl).