Issue 22, 2001

First chiral selenium ylides used for asymmetric conversion of aldehydes into epoxides

Abstract

Enantioenriched selenonium ylides have been generated by

addition of benzyl bromide to C2 symmetric (2R,5R)-2,5-dimethylselenolane in the presence of NaOH, and subsequently reacted with a variety of aldehydes to give oxiranes with excellent enantiomeric excesses (a catalytic version has been achieved); also, an aliphatic cyclic hypervalent dibromoselenurane structure has been demonstrated by X-ray analysis.

Supplementary files

Article information

Article type
Communication
Submitted
09 Jul 2001
Accepted
08 Oct 2001
First published
26 Oct 2001

Chem. Commun., 2001, 2350-2351

First chiral selenium ylides used for asymmetric conversion of aldehydes into epoxides

H. Takada, P. Metzner and C. Philouze, Chem. Commun., 2001, 2350 DOI: 10.1039/B106063P

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