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

doi:10.1055/s-2008-1042938

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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;

Abstract

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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.

Key words

β-seleno amines - allylic alkylation - oxazolidinone ring-opening - asymmetric catalysis

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

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