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Synlett 2012; 23(5): 796-800
DOI: 10.1055/s-0031-1290303
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© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Synthesis of Enantioenriched β-Arylsplitomicins

Ji-Yu Wang
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China, Fax: +86(28)85257883   Email: xmzhang@cioc.ac.cn
b   Graduate School of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Hui Zhang
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China, Fax: +86(28)85257883   Email: xmzhang@cioc.ac.cn
b   Graduate School of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Yu-Hua Liao
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China, Fax: +86(28)85257883   Email: xmzhang@cioc.ac.cn
b   Graduate School of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Wei-Cheng Yuan
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China, Fax: +86(28)85257883   Email: xmzhang@cioc.ac.cn
,
Yu-Jun Feng*
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China, Fax: +86(28)85257883   Email: xmzhang@cioc.ac.cn
,
Xiao-Mei Zhang*
a   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China, Fax: +86(28)85257883   Email: xmzhang@cioc.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 02 December 2011

Accepted: 09 January 2012

Publication Date:
16 February 2012 (online)

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Abstract

By employing a chiral bifunctional thiourea–tertiary amine as catalyst, domino Michael-type Friedel–Crafts alkylation/cyclization of β-naphthols with akylidene Meldrum’s acids was realized. The reactions afforded various enantioenriched β-arylsplitomicins with good yields (up to 99%) in moderate enantio­selectivities (up to 79%).

Key words

domino reaction - alkylation - cyclization - phenols - organocatalysis - asymmetric catalysis

Supporting Information

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

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