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Stereoselective Hydrocyanation of Alkenyl Sulfoxides as a Method to Highly Enantiomerically Enriched Compounds with Tertiary and Quaternary Chiral Carbon Atoms
Author(s) -
García Ruano Jose L.,
Cifuentes García Marta,
Laso Nieves M.,
Martín Castro Ana M.,
Rodríguez Ramos Jesús H.
Publication year - 2001
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 - 10.1002/1521-3773(20010702)40:13<2507::aid-anie2507>3.0.co;2-r
Subject(s) - hydrocyanation , chemistry , stereoselectivity , quaternary carbon , alkylation , carbon fibers , enantioselective synthesis , organic chemistry , nitrile , stereochemistry , medicinal chemistry , catalysis , computer science , composite number , algorithm
Terminal alkynes are easily transformed into enantiomerically enriched compounds containing tertiary and quaternary carbon atoms. Sulfinylation followed by reduction (or alkylation) and hydrocyanation of the resulting vinyl sulfoxides with Et 2 AlCN provides nitriles bearing the chiral center, which can in turn undergo reaction to form the desired products (see reaction scheme). Tol=4‐tolyl.