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Enantioselective Strecker and Allylation Reactions With Aldimines Catalyzed by Chiral Oxazaborolidinium Ions

Ki-Tae Kang, Sang Hyun Park, Do Hyun Ryu

Org Lett. 2019 Sep 6;21(17):6679-6683.

PMID: 31429578

Abstract:

Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yield (up to 98%) with high to excellent enantioselectivity (up to 99% ee). A rational mechanistic model for the complex of COBI and aldimine is provided to account for these enantioselective reactions.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP2179922 Tributyltin cyanide Tributyltin cyanide 2179-92-2 Price
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