Highly Enantioselective Synthesis of Chiral γ‑Lactams by Rh-Catalyzed Asymmetric Hydrogenation

A Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system has been identified for the straightforward asymmetric synthesis of chiral γ-lactams. A variety of NH free α,β-unsaturated lactams bearing a β-aryl or β-alkyl substituent were smoothly hydrogenated to provide the desired γ-lactams in up to 99% y...

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Bibliographic Details
Published in:ACS catalysis 2018-06, Vol.8 (6), p.4824-4828
Main Authors: Lang, Qiwei, Gu, Guoxian, Cheng, Yaoti, Yin, Qin, Zhang, Xumu
Format: Article
Language:English
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Summary:A Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system has been identified for the straightforward asymmetric synthesis of chiral γ-lactams. A variety of NH free α,β-unsaturated lactams bearing a β-aryl or β-alkyl substituent were smoothly hydrogenated to provide the desired γ-lactams in up to 99% yield and 99% enantiomeric excess (ee). This methodology provides a highly practical pathway to synthesize chiral γ-lactams or γ-amino acids.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b00827