Synthesis 2009(23): 4015-4021  
DOI: 10.1055/s-0029-1217029
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Cerium(III)-Mediated Efficient and Stereoselective Hydrochalcogenation of Terminal Alkynes

Claudio C. Silveira*, Samuel R. Mendes, Daniel D. Rosa, Gilson Zeni
Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil
Fax: +55(55)32208754; e-Mail: silveira@quimica.ufsm.br;
Further Information

Publication History

Received 15 May 2009
Publication Date:
12 October 2009 (online)

Abstract

Vinylic chalcogenides were synthesized stereospecifically by hydrochalcogenation of propargylic amines or alcohols mediated by cerium(III) chloride. The products were obtained in good yields and with high regio- and stereoselectivities.

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One equivalent of MeOH was used for the cleavage of diphenyl diselenide.