Synlett 2005(6): 0939-0942  
DOI: 10.1055/s-2005-864815
LETTER
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of Trisubstituted Tetrahydropyrans from Baylis-Hillman Derivatives via n-Bu3SnH-Mediated 6-Endo/6-Exo-trig Vinyl Radical Cyclization

Ponnusamy Shanmugam*, Paramasivan Rajasingh
Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum-695 019, India
Fax: +91(471)2491712; e-Mail: shanmu196@rediffmail.com;
Further Information

Publication History

Received 22 December 2004
Publication Date:
23 March 2005 (online)

Abstract

The stereoselective 6-endo- and 6-exo-trig cyclization of propargyl and phenyl homopropargyl derivatives of Baylis-­Hillman adducts by the use of n-Bu3SnH-mediated vinyl radical ­cyclization afforded poly-substituted functionalized tetrahydro­pyrans in good yield.