Regiodivergent Ring Opening of Chiral Aziridines

Kinetic resolution of strained three-membered rings has proven broadly useful for the generation of enantiopure organic intermediates. Herein we demonstrate a complementary approach whereby a single catalyst transforms a racemic mixture of aziridines to a pair of regioisomeric products, each in good...

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Bibliographic Details
Published in:Science (American Association for the Advancement of Science) 2009-12, Vol.326 (5960), p.1662-1662
Main Authors: Wu, Bin, Parquette, Jon R, RajanBabu, T.V
Format: Article
Language:English
Subjects:
Azides
Aziridines
Brevia
Catalysis
Catalysts
Chemical compounds
Chemical reactions
Chemistry
Enantiomers
Exact sciences and technology
General and physical chemistry
Kinetics
Materials
Molecular structure
Organic chemistry
Reagents
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Kinetic resolution of strained three-membered rings has proven broadly useful for the generation of enantiopure organic intermediates. Herein we demonstrate a complementary approach whereby a single catalyst transforms a racemic mixture of aziridines to a pair of regioisomeric products, each in good yield with exceptionally high enantioselectivity. Specifically, the dimeric yttrium salen catalyst accelerates the ring opening of aliphatic aziridines by trimethylsilylazide, inducing nucleophilic attack at the primary position of one enantiomer and the secondary position of the other. Both rate and selectivity are highly sensitive to the catalyst structure.
ISSN:0036-8075
1095-9203
DOI:10.1126/science.1180739