Synthesis 2008(8): 1262-1268  
DOI: 10.1055/s-2008-1042938
PAPER
© Georg Thieme Verlag Stuttgart · New York

Modular Synthesis of Chiral N-Protected β-Seleno Amines and Amides via Cleavage of 2-Oxazolidinones and Application in Palladium-Catalyzed Asymmetric­ Allylic Alkylation

Jasquer A. Sehnem, Fabrício Vargas, Priscila Milani, Vanessa Nascimento, Antonio L. Braga*
Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil
Fax: +55(55)32208998; e-Mail: albraga@quimica.ufsm.br;
Further Information

Publication History

Received 16 November 2007
Publication Date:
18 March 2008 (online)

Abstract

A set of chiral β-seleno amines have been efficiently synthesized via the ring-opening reaction of chiral N-acyl oxazolidin­ones by selenium nucleophiles. These compounds could be transformed into β-seleno amides by reaction with acid chlorides. The present method is applicable to the synthesis of β-chalcogeno amides containing selenium, sulfur and tellurium atoms in good yields. Additionally, these new compounds were evaluated as ligands in the palladium-catalyzed asymmetric allylic alkylation, giving the corresponding alkylated products in up to 98% ee.