Chiral Bases as Useful Probes of Lithium Amide Reactivity | Zendy

Prestly Mark R. | Zendy; Simpkins Nigel S. | Zendy

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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.

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