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Forming Tertiary Organolithiums and Organocuprates from Nitrile Precursors and their Bimolecular Reactions with Carbon Electrophiles to Form Quaternary Carbon Stereocenters
Author(s) -
Schnermann Martin J.,
Untiedt Nicholas L.,
JiménezOsés Gonzalo,
Houk Kendall N.,
Overman Larry E.
Publication year - 2012
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.201205001
Subject(s) - stereocenter , electrophile , chemistry , nitrile , carbon fibers , polymer chemistry , organic chemistry , enantioselective synthesis , catalysis , materials science , composite number , composite material
Unstabilized tertiary organolithium intermediates are conveniently generated by reductive decyanation of nitriles, and these reagents and their derived cuprates couple in useful yields with carbon‐ centered electrophiles (see example). Chiral tertiary organolithium and organocuprate derivatives of substituted cis‐ perhydroazulenes and cis ‐perhydropentalenes react with electrophiles with high diastereoselectivity from the more‐hindered concave face.