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Simple and Efficient Asymmetric α‐Alkylation and α,α‐Bisalkylation of Acyclic Ketones by Using Chiral N‐Amino Cyclic Carbamate Hydrazones
Author(s) -
Lim Daniel,
Coltart Don M.
Publication year - 2008
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.200800848
Subject(s) - lithium diisopropylamide , stereoselectivity , chemistry , alkylation , selectivity , carbamate , lithium (medication) , combinatorial chemistry , organic chemistry , catalysis , biology , ion , deprotonation , endocrinology
Distinguishing left from right : In the title reactions, chiral N‐amino cyclic carbamates (ACCs) substantially diminish the drawbacks associated with the use of chiral dialkyl hydrazines, yet provide excellent stereoselectivity and high yields. In addition, ACCs exhibit a unique directing effect that overrides the inherent selectivity of lithium diisopropylamide (LDA) and enables the asymmetric α,α‐bisalkylation of ketones (see scheme).