First chiral selenium ylides used for asymmetric conversion of aldehydes into epoxides.
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.
Takada
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H
Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), ISMRA-Université, 6, boulevard du Maréchal Juin, 14050 Caen, France.
Metzner
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P
Philouze
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C