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2005
Organo-silicon compounds
S 0060
Silylene Transfer to Carbonyl Compounds and Subsequent Ireland—Claisen
to Control Formation of Quaternary Carbon Stereocenters. —
27- 165 Rearrangements
The silver-catalyzed silylene transfer of silacyclopropane (II) to a range of α,β-unsaturated carbonyl compounds demonstrates that both the carbonyl group and the C=C
double bond of these compounds react to afford oxasilacyclopentene products. These
compounds can undergo facile and selective Ireland—Claisen rearrangements as in the
case of products (VII) and (IX), and aldol reactions exemplified by formation of compounds (XII)/(XII) and (XIV), with formation of multiple contiguous stereocenters and
quaternary carbon centers. — (CALAD, S. A.; WOERPEL*, K. A.; J. Am. Chem.
Soc. 127 (2005) 7, 2046-2047; Dep. Chem., Univ. Calif., Irvine, CA 92717, USA;
Eng.) — Klein
2005
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