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Org Biomol Chem. 2017 Apr 05;15(14):3006-3012. doi: 10.1039/c7ob00442g.

Synthesis of chiral cyclic amines via Ir-catalyzed enantioselective hydrogenation of cyclic imines.

Organic & biomolecular chemistry

Ying Zhang, Duanyang Kong, Rui Wang, Guohua Hou

Affiliations

  1. Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, No. 19 Xinjiekouwai St., Beijing 100875, China. [email protected].

PMID: 28294268 DOI: 10.1039/c7ob00442g

Abstract

A highly enantioselective hydrogenation of cyclic imines for synthesis of chiral cyclic amines has been realized. With the complex of iridium and (R,R)-f-spiroPhos as the catalyst, a range of cyclic 2-aryl imines were smoothly hydrogenated under mild conditions without any additive to provide the corresponding chiral cyclic amines with excellent enantioselectivities of up to 98% ee. Moreover, this method could be successfully applied to the synthesis of (+)-(6S,10bR)-McN-4612-Z.

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