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Chiral Bases as Useful Probes of Lithium Amide Reactivity
Author(s) -
Prestly Mark R.,
Simpkins Nigel S.
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.201206558
Subject(s) - lithium diisopropylamide , lithium (medication) , amide , lithium amide , keto–enol tautomerism , chemistry , organic chemistry , stereochemistry , combinatorial chemistry , enantioselective synthesis , psychology , deprotonation , catalysis , psychiatry , ion
Experiments involving competition between chiral and achiral lithium amides provide a qualitative impression of the kinetics of different amide motifs in enolization reactions. The level of enantioselectivity was not diminished by the inclusion of lithium diisopropylamide (LDA; see scheme) into asymmetric enolizations mediated by a chiral lithium amide base, derived from a 1,2‐diamine.