Tandem SmI2-induced nitrone beta-elimination/aldol-type reaction.
Upon treatment with SmI(2), the carbohydrate-derived nitrones 1a,b undergo a beta-elimination of the benzyloxy group at C-1, forming original samarium(III) oxy-enamine intermediates. The latter can be reacted with carbonyl compounds to produce aldol-type adducts. The tandem process results in the transformation of a C-O bond into a C-C bond.
Racine
Emilie
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Département de Chimie Moléculaire (SERCO) UMR-5250, ICMG FR-2607, CNRS-Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 09, France.
Py
Sandrine
S