title: Kinetic Resolution of Azomethine Imines by Brønsted Acid Catalyzed Enantioselective Reduction.
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.
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, 10 Marie Curie, Ottawa, Ontario, K1N 6N5 (Canada).
authors.forename: Amanda
authors.initials: A
authors.lastname: Bongers
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, 10 Marie Curie, Ottawa, Ontario, K1N 6N5 (Canada).
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Moon
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, 10 Marie Curie, Ottawa, Ontario, K1N 6N5 (Canada). andre.beauchemin@uottawa.ca.
authors.forename: André M
authors.initials: AM
authors.lastname: Beauchemin
keywords: Brønsted acids; asymmetric catalysis; azo compounds; kinetic resolution; reduction