Abstract
Reaction of 1,2-cyclopropanated sugars with a catalytic amount
ofZeise's dimer [Pt(C2H4)Cl2]2 and an alcohol gives 2-C-branched
glycosides by a novel platinum catalyzed ring-opening. A wide
variety of alcohols can participate in this ring-opening reaction
giving 2-C-branched glycosides ranging from methyl glycosides to
complex disaccharides (17 examples). Very high
diastereoselectivity is obtained at the newly formed C-1
stereocenter strongly favoring the alfa-glycoside. The mechanism
presumably involves the formation of an intermediate
platinacyclobutane which undergoes ring-opening at C-1 by the
alcohol followed by reductive elimination of platinum.
Original language | English |
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Journal | Journal of the American Chemical Society |
Volume | 120 |
Issue number | 46 |
Pages (from-to) | 12137-12138 |
ISSN | 0002-7863 |
Publication status | Published - 1998 |