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Titanocene(III) Chloride Mediated Stereoselective Synthesis of Trisubstituted Tetrahydrofurans and a Spirolactone by Tandem Radical Reactions
Author(s) -
Mukherjee Shirshendu,
Roy Rajdip,
Chandra Roy Subhas
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400097
Subject(s) - chemistry , tetrahydrofuran , stereoselectivity , adduct , epoxide , tandem , medicinal chemistry , radical cyclization , chloride , zinc , organic chemistry , stereochemistry , catalysis , materials science , solvent , composite material
Abstract The titanocene(III) chloride (Cp 2 TiCl) mediated stereoselective synthesis of highly substituted tetrahydrofurans has been achieved by a reaction that proceeds through a tandem radical cyclization reaction between a Baylis–Hillman adduct and an activated bromo/iodo compound. The reaction of an epoxide with the Baylis–Hillman adduct furnished a spirolactone through a radical cyclization followed by an in situ lactonization. Cp 2 TiCl was prepared in situ from commercially available Cp 2 TiCl 2 and zinc dust in tetrahydrofuran.