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

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

doi:10.1021/jacs.9b07418

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

J Am Chem Soc. 2019 Oct 16;141(41):16362-16373. doi: 10.1021/jacs.9b07418. Epub 2019 Oct 8.

Authors

Mingyue Wu¹, Zhaobin Han², Kaizhi Li¹, Ji'en Wu¹, Kuiling Ding², Yixin Lu^{1

3

4}

Affiliations

¹ Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543.
² State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , PR China.
³ Joint School of National University of Singapore and Tianjin University , International Campus of Tianjin University , Binhai New City , Fuzhou, Fujian 359297 , PR China.
⁴ National University of Singapore (Suzhou) Research Institute , 377 Lin Quan Street, Suzhou Industrial Park , Suzhou , Jiangsu 215123 , PR China.

PMID: 31545594
DOI: 10.1021/jacs.9b07418

Abstract

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 γ-substituted allenoates catalyzed by NUSIOC-Phos has been disclosed. Diastereospecific tricyclic γ-lactams containing five contiguous stereogenic centers were obtained in high yields and with nearly perfect enantioselectivities. A kinetic resolution process of racemic γ-substituted allenoates was developed for the generation of optically enriched chiral allenoates.

Publication types

Research Support, Non-U.S. Gov't