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Asymmetric Reductive Amination with Pinacolborane Catalyzed by Chiral SPINOL Borophosphates

Zhenwei Wu, Hualing He, Minglei Chen, Linfei Zhu, Weitao Zheng, Yang Cao, Jon C. Antilla

2022Organic Letters15 citationsDOI

Abstract

The catalytic asymmetric reductive amination of ketones with pinacolborane employing chiral SPINOL-derived borophosphates as catalysts has been realized. A series of chiral amine derivatives bearing multiple functional groups were obtained in good to excellent yields and enantioselectivities (up to 97% yield, 98% ee) under mild reaction conditions. Moreover, the synthetic applicability of the established method has been demonstrated by the asymmetric synthesis of (R)-Fendiline.

Topics & Concepts

ChemistryAminationYield (engineering)CatalysisReductive aminationAmine gas treatingOrganic chemistryCombinatorial chemistryMaterials scienceMetallurgyAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisAsymmetric Synthesis and Catalysis