Synlett 2011(9): 1296-1302  
DOI: 10.1055/s-0030-1260557
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

First Friedel-Crafts Reaction of the Baylis-Hillman Adducts Derived from Nitroolefins: Application towards Synthesis of Pyrrolidines and Spiropyrrolidines

Manickam Bakthadoss*, Nagappan Sivakumar
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Fax: +91(44)22352494; e-Mail: bhakthadoss@yahoo.com;
Further Information

Publication History

Received 17 December 2010
Publication Date:
16 May 2011 (online)

Abstract

A general and simple protocol for the arylation of ­Baylis-Hillman adducts derived from nitroolefins leading to novel classes of (E)-2-nitro-1,3-diarylprop-1-enes and 1-[(E)-2-nitro-3-arylallyl]naphthalenes via an intermolecular Friedel-Crafts reaction have been achieved. Further application of these compounds has been demonstrated for the synthesis of pyrrolidines and 3-spiropyrrolidines which are integral components of many natural products and bioactive molecules.

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