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- Title
Kinetic Resolution of Azomethine Imines by Brønsted Acid Catalyzed Enantioselective Reduction.
- Authors
Bongers, Amanda; Moon, Patrick J.; Beauchemin, André M.
- Abstract
Azomethine imines are valuable substrates in asymmetric catalysis, and can be precursors to β-amino carbonyl compounds and complex hydrazines. However, their utility is limited because complex and enantioenriched azomethine imines are often unavailable. Reported herein is a kinetic resolution of N,N′-cyclic azomethine imines by enantioselective reduction (s=13–43). This resolution was accomplished using a Brønsted acid catalyst, and represents the first example of the asymmetric reduction of azomethine imines. The pyrazolidinone product (up to 86 % ee) and the recovered azomethine imine (up to 99 % ee) can both be used to access the opposite enantiomers of valuable products.
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 51, p15736
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201507548