One-Pot Synthesis of New Chiral Sulfides and Selenides Containing Oxazolidines­: Catalyst in the Enantioselective Addition of Diethylzinc to Benzaldehyde­

Antonio L.  Braga; Oscar E. D.  Rodrigues; Marcio W.  Paixão; Helmoz R.  Appelt; Claudio C.  Silveira; Diana P.  Bottega

doi:10.1055/s-2002-35225

SHORTPAPER

One-Pot Synthesis of New Chiral Sulfides and Selenides Containing Oxazolidines: Catalyst in the Enantioselective Addition of Diethylzinc to Benzaldehyde

Antonio L. Braga*^a, Oscar E. D. Rodrigues^a, Marcio W. Paixão^a, Helmoz R. Appelt^b, Claudio C. Silveira^a, Diana P. Bottega^a
^a Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil
e-Mail: albraga@quimica.ufsm.br;
^b Centro Universitário Franciscano, Rua dos Andradas, 1614 - Centro 97010-032, Santa Maria, RS, Brazil

Abstract

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Abstract

A new easily accessible class of chiral sulfides 1 and selenides 2 containing oxazolidine was prepared from amino acids. They were used as chiral ligands in the catalytic asymmetric addition of diethylzinc to benzaldehyde to give the corresponding secondary alcohols in up to 80% ee with an R-configuration.

Key words

sulfur - selenium - stereoselective synthesis - asymmetric catalysis - zinc

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References

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One-Pot Synthesis of New Chiral Sulfides and Selenides Containing Oxazolidines­: Catalyst in the Enantioselective Addition of Diethylzinc to Benzaldehyde­

One-Pot Synthesis of New Chiral Sulfides and Selenides Containing Oxazolidines: Catalyst in the Enantioselective Addition of Diethylzinc to Benzaldehyde