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Synthesis 2009(9): 1551-1556  
DOI: 10.1055/s-0029-1216638
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Oxidations of Electron-Poor Alkenes Promoted by the β-Amino Alcohol/TBHP System

Alessio Russo, Alessandra Lattanzi*
Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, 84084 Fisciano, Italy
Fax: +39(89)969603; e-Mail: lattanzi@unisa.it;
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Publication History

Received 16 February 2009
Publication Date:
14 April 2009 (online)

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Abstract

The asymmetric oxyfunctionalization of alkenes is a fundamental process in synthetic organic chemistry. In this contribution, we review our findings on the enantioselective organocatalyzed oxidation of electron-poor alkenes. Readily or commercially available β-amino alcohols displayed catalytic activity in the asymmetric epoxidation of α,β-enones and β-peroxidation of nitroalkenes with tert-butyl hydroperoxide (TBHP) as the oxidant. The corresponding epoxides and peroxides were isolated in good to high yield and enantioselectivity.

Key words

α,β-enones - epoxides - peroxides - α,α-diaryl-l-prolinols - nitroalkenes

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