Synthesis 2013; 45(5): 601-608
DOI: 10.1055/s-0032-1318200
paper
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of Highly Substituted Chromans by a Zinc(II)-Catalyzed Tandem Friedel–Crafts Alkylation/Michael Addition Reaction

Chao Li, Feng-Lei Liu, You-Quan Zou, Liang-Qiu Lu, Jia-Rong Chen, Wen-Jing Xiao*
  • Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China   Fax: +86(27)67862041   Email: wxiao@mail.ccnu.edu
Further Information

Publication History

Received: 12 December 2012

Accepted after revision: 20 January 2013

Publication Date:
05 February 2013 (eFirst)

Abstract

An enantioselective tandem Friedel–Crafts alkylation/ Michael addition reaction of 1-methylindoles with nitroolefin enoates catalyzed by a chiral tridentate bisoxazoline-Zn(II) complex has been described. This method provides an efficient route to highly substituted chromans in good isolated yields with high stereoselectivities (up to 95:5 dr and 91% ee).

Supporting Information