Cyclohexyl-Fused, Spirobiindane-Derived, Phosphine-Catalyzed Synthesis of Tricyclic Î³-Lactams and Kinetic Resolution of Î³-Substituted Allenoates.

Wu, Mingyue; Han, Zhaobin; Li, Kaizhi; Wu, Ji'en; Ding, Kuiling; Lu, Yixin

Wu, Mingyue; Han, Zhaobin; Li, Kaizhi; Wu, Ji'en; Ding, Kuiling; Lu, Yixin.

Afiliación

Wu M; Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543.
Han Z; State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , PR China.
Li K; Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543.
Wu J; Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543.
Ding K; State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , PR China.
Lu Y; Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543.

J Am Chem Soc ; 141(41): 16362-16373, 2019 10 16.

Article en En | MEDLINE | ID: mdl-31545594

RESUMEN

A C2-symmetric chiral phosphine catalyst, NUSIOC-Phos, which can be easily derived from cyclohexyl-fused spirobiindane, was introduced. A highly enantioselective domino process involving pyrrolidine-2,3-diones and Î³-substituted allenoates catalyzed by NUSIOC-Phos has been disclosed. Diastereospecific tricyclic Î³-lactams containing five contiguous stereogenic centers were obtained in high yields and with nearly perfect enantioselectivities. A kinetic resolution process of racemic Î³-substituted allenoates was developed for the generation of optically enriched chiral allenoates.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2019 Tipo del documento: Article Pais de publicación: Estados Unidos

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