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Synlett 2011(9): 1239-1242  
DOI: 10.1055/s-0030-1260537
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© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of Tetrahydropyrano[3,4-b]indoles Catalyzed by Chiral N-Triflyl Phosphoramide via Intramolecular Friedel-Crafts Alkylation Reaction

Jun-Wei Zhanga,b, Quan Caib, Xiao-Xin Shia, Wei Zhangb, Shu-Li You*a,b
a School of Pharmacy, East China University of Science and Technology, 130 Mei-Long Road, Shanghai 200237, P. R. of China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China
Fax: (+86) 21-54925087; e-Mail: slyou@sioc.ac.cn;
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Publication History

Received 30 January 2011
Publication Date:
20 April 2011 (online)

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Abstract

A highly efficient intramolecular enantioselective Friedel-Crafts alkylation reaction of indolyl enones utilizing chiral N-triflyl phosphoramide catalyst is described. Various tetrahydropyrano[3,4-b]indoles (THPI) have been afforded with excellent yields and up to 98% ee.

Key words

asymmetric catalysis - chiral Brønsted acids - N-triflyl phosphoramide - Friedel-Crafts - indoles

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