Synlett 2014; 25(6): 805-808
DOI: 10.1055/s-0033-1340825
letter
© Georg Thieme Verlag Stuttgart · New York

Concise Synthesis of Chiral N-Benzyl-α,α-Diarylprolinols through Shi Asymmetric Epoxidation

Jie Li
a   College of Chemistry and Materials Engineering, Quzhou University, Quzhou 324000, P. R. of China   Fax: +86(570)8015339   Email: gechengsheng@qzu.zj.cn
,
Hai Zhou
a   College of Chemistry and Materials Engineering, Quzhou University, Quzhou 324000, P. R. of China   Fax: +86(570)8015339   Email: gechengsheng@qzu.zj.cn
,
Jiangsen Weng
a   College of Chemistry and Materials Engineering, Quzhou University, Quzhou 324000, P. R. of China   Fax: +86(570)8015339   Email: gechengsheng@qzu.zj.cn
,
Mingwen Wang
b   ACS Scientific Inc., Metuchen, NJ 08840, USA
,
Chengsheng Ge*
a   College of Chemistry and Materials Engineering, Quzhou University, Quzhou 324000, P. R. of China   Fax: +86(570)8015339   Email: gechengsheng@qzu.zj.cn
,
Wujie Tu
a   College of Chemistry and Materials Engineering, Quzhou University, Quzhou 324000, P. R. of China   Fax: +86(570)8015339   Email: gechengsheng@qzu.zj.cn
› Author Affiliations
Further Information

Publication History

Received: 05 December 2013

Accepted after revision: 22 January 2014

Publication Date:
11 March 2014 (online)


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Abstract

A concise and practical synthesis of chiral N-benzyl-α,α-diaryl-2-prolinols was developed through Shi asymmetric epoxidation, followed by double nucleophilic substitution of bromo-containing olefins. A series of enantioenriched N-benzyl-α,α-diaryl-2-prolinols were obtained with excellent enantioselectivities (96% ee) in moderate to good yields (40–76% yield). For the first time, enantiopure N-benzyl-α,α-diphenyl-2-prolinol was obtained from bromo-containing olefin using this methodology.

Supporting Information