Synthesis 2008(12): 1943-1947  
DOI: 10.1055/s-2008-1067049
PAPER
© Georg Thieme Verlag Stuttgart · New York

Boron Trifluoride-Diethyl Etherate Complex Mediated Allylation of Baylis-Hillman Adducts: A Facile Synthesis of 1,5-Dienes

Jhillu S. Yadav*, Basi V. Subba Reddy, Satadru S. Mandal, Ashutosh Pratap Singh, Ashok K. Basak
Division of Organic Chemistry I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
Further Information

Publication History

Received 27 February 2008
Publication Date:
29 April 2008 (online)

Abstract

Morita-Baylis-Hillman adducts undergo smooth allylic nucleophilic substitution (SN2′) with allyltrimethylsilane in the presence of BF3·OEt2 under mild reaction conditions to afford 1,5-diene derivatives in good yields with high selectivity.