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Synlett 2014; 25(6): 805-808
DOI: 10.1055/s-0033-1340825
DOI: 10.1055/s-0033-1340825
letter
Concise Synthesis of Chiral N-Benzyl-α,α-Diarylprolinols through Shi Asymmetric Epoxidation
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Publication History
Received: 05 December 2013
Accepted after revision: 22 January 2014
Publication Date:
11 March 2014 (online)


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.
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- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
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