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Publication 147
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P. Müller, D. Fernandez, P. Nury, J.-C. Rossier,
“Transition-Metal-Catalyzed Carbenoid Reactions of Sulfonium Ylides”
Helv. Chim. Acta 1999, 82, 935-945.
Olefins undergo cyclopropanation with diphenylsulfonium (ethoxycarbonyl)methylide (=diphenylsulfonium 2-ethoxy-2-oxoethylide; 3a) in the presence of chiral CuI or RhII catalysts. trans/cis Ratios and ee's of the cyclopropanes 6 obtained with this ylide in the presence of a chiral CuI catalyst 7 are identical with those obtained with ethyl diazoacetate (4). In the case of catalysis with RhII, the trans/cis ratios of the cyclopropanes as well as the enantioselectivity change slightly upon going from the ylide 3a to diazoacetate 4.
DOI : 10.1002/(SICI)1522-2675(19990609)82:6<935::AID-HLCA935>3.0.CO;2-X
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