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Synthesis 2009(9): 1551-1556
DOI: 10.1055/s-0029-1216638
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
Further Information
Received
16 February 2009
Publication Date:
14 April 2009 (online)
Publication History
Publication Date:
14 April 2009 (online)
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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