Synlett 2013; 24(4): 437-442
DOI: 10.1055/s-0032-1318145
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© Georg Thieme Verlag Stuttgart · New York

Chiral NHC/Cu(I)-Catalyzed Asymmetric Hydroboration of Aldimines: Enantioselective Synthesis of α-Amido Boronic Esters

Shu-Sheng Zhang
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166263   eMail: tianping@sioc.ac.cn   eMail: lingq@sioc.ac.cn
,
Yi-Shuang Zhao
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166263   eMail: tianping@sioc.ac.cn   eMail: lingq@sioc.ac.cn
,
Ping Tian*
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166263   eMail: tianping@sioc.ac.cn   eMail: lingq@sioc.ac.cn
,
Guo-Qiang Lin*
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166263   eMail: tianping@sioc.ac.cn   eMail: lingq@sioc.ac.cn
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Publikationsverlauf

Received: 07. Dezember 2012

Accepted after revision: 10. Januar 2013

Publikationsdatum:
29. Januar 2013 (online)


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Abstract

Non-C 2-symmetric (N-alkyl, N-aryl)-hybrid chiral NHC/Cu(I) complex catalyzed asymmetric hydroboration of N-benzoyl aldimines has been developed. The reaction proceeded smoothly at room temperature, giving α-amido boronic esters in excellent yields (up to 94%) and good enantioselectivities (up to 86% ee).

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