Titanocene(III) Chloride Mediated Stereoselective Synthesis of Trisubstituted Tetrahydrofurans and a Spirolactone by Tandem Radical Reactions | Zendy

Mukherjee Shirshendu | Zendy; Roy Rajdip | Zendy; Chandra Roy Subhas | Zendy

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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

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.

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