PALLADIUM-MEDIATED ARYLATION OF ACETYLATED ENONES DERIVED FROM GLYCALS .4. SYNTHESIS OF ARYL 2-DEOXY-BETA-D-C-GLYCOPYRANOSIDES

被引:52
作者
BENHADDOU, R [1 ]
CZERNECKI, S [1 ]
VILLE, G [1 ]
机构
[1] UNIV PARIS 06,CHIM GLUCIDES LAB,TOUR 74,E6,4 PL JUSSIEU,F-75230 PARIS 05,FRANCE
关键词
D O I
10.1021/jo00043a016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-mediated arylation of the peracetylated glycal-derived enones 1, 2, and 3 afforded mixtures of C-glycosides containing an arylated enone (1a, 2a, or 3a) and an arylated ketone (1b, 2b, or 3b). A rationale for the formation of these compounds is given. Reduction of the arylated enones proceeds in a stereospecific manner, thus affording aryl 2-deoxy-beta-D-C-glycopyranosides in high yield.
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页码:4612 / 4616
页数:5
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