Affiliation:
1. Key Laboratory of Green Chemistry & Technology of Ministry of Education College of Chemistry Sichuan University 29 Wangjiang Road Chengdu 610064 P. R. China
Abstract
AbstractWe herein demonstrated an organocatalytic asymmetric Mannich/radical debromination cascade of α‐brominated ketones. With this protocol, a diversity of chiral β‐amino ketone‐pyrazolinone scaffolds, which have important versatilities in medicine and chemical synthesis, were constructed in high yields (up to 94%) with excellent enantioselectivities (up to 99% ee). This methodology features mild reaction conditions, broad substrate scope, and high functional group tolerance. Moreover, mechanistic investigations revealed that this cascade reaction proceeds through a bifunctional phosphonium salt‐catalyzed Mannich reaction of α‐brominated ketones with pyrazolinone ketimines, which is followed by an oxygen‐induced radical debromination. This protocol represents a novel activation mode for α‐brominated ketones and opens new avenues for catalytic enantioselective radical reactions under ion‐pair system.
Funder
National Natural Science Foundation of China
Beijing National Laboratory for Molecular Sciences
Fundamental Research Funds for the Central Universities
Cited by
3 articles.
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