Premium
Synthesis of C ‐Glycosides and C ‐Disaccharides using Mukaiyama Aldol Reaction in Aqueous Media
Author(s) -
Zeitouni Jennifer,
Norsikian Stéphanie,
Merlet Denis,
Lubineau André
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606113
Subject(s) - aldol reaction , chemistry , enol , trimethylsilyl , diastereomer , enol ether , organic chemistry , yield (engineering) , aqueous solution , ketone , aldol condensation , medicinal chemistry , catalysis , materials science , metallurgy
We describe here a new strategy for the preparation of C ‐glycosides and C ‐disaccharides in the aqueous phase using the Mukaiyama aldol reaction. We first studied the reaction between formyl‐2,3,4,6‐tetra‐ O ‐benzyl‐β‐ D ‐glucopyranoside 1 and the trimethylsilyl enol ether 2 derived from acetophenone. Using Yb(OTf) 3 (10 mol %) as catalyst in a mixture of THF/water at room temperature, the enol adducts were isolated in a high (90 %) yield but with a moderate diastereoselectivity. The reaction can also be performed in pure THF leading to a single diastereoisomer but in a much lower yield (56 %). The aldol reaction was then applied to the synthesis of C ‐disaccharides using the trimethylsilyl enol ether 10 derived from the functionalized ketone 9 . In both the aqueous phase and in anhydrous THF, the reaction can be achieved in high yields giving in each case only two aldol products out of the four possible diastereoisomers.