Journal ArticleDOI
Highly stereoselective C-allylation of glycopyranosides with allylsilanes catalyzed by silyl triflate or iodosilane
Reads0
Chats0
TLDR
In this paper, it was shown that α-D-glycopyranosyl chlorides readily undergo allylation with allylsilanes catalyzed by trimethylsilyl triflate or iodotrimethylsilane in a highly stereoselective mode.About:
This article is published in Tetrahedron Letters.The article was published on 1984-01-01. It has received 103 citations till now. The article focuses on the topics: Trifluoromethanesulfonate.read more
Citations
More filters
Journal ArticleDOI
Recent Advances in the Chemical Synthesis of C-Glycosides
TL;DR: Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor.
Journal ArticleDOI
Carbon-carbon bond forming reactions mediated by silicon Lewis acids.
Alexander D. Dilman,S. L. Ioffe +1 more
Journal ArticleDOI
Total Synthesis of Leucascandrolide A
TL;DR: Leucascandrolide A (I), a polyoxygenated marine macrolide of a new genus (Scheme I), was isolated in 1996 by Pietra and co-workers from the calcareous sponge Leucascandra caveolata.
Journal ArticleDOI
Stereoselective C-glycosylation reactions of pyranoses: the conformational preference and reactions of the mannosyl cation.
Claudia G. Lucero,K. A. Woerpel +1 more
TL;DR: An analysis of the conformational preferences of the intermediate oxocarbenium ions, including the mannosyl cation, as well as consideration of steric effects that develop in the transition states for nucleophilic attack provide explanations for these phenomena.
References
More filters
Journal ArticleDOI
Highly stereoselective approaches to .alpha.- and .beta.-C-glycopyranosides
Journal ArticleDOI
Trimethysilyl triflate in organic synthesis11Part 11 of this series. Part 10: S. Murata and R. Noyori, Tetrahedron Letters 2107 (1981).
TL;DR: Trimethylsilyl triflate is a powerful silylating agent for organic compounds and acts as a catalyst which accelerates a variety of nucleophilic reactions in aprotic media as discussed by the authors.
Journal ArticleDOI
REACTIONS OF ALLYLSILANES AND APPLICATION TO ORGANIC SYNThESIS
TL;DR: In this article, the double bond of allylsilanes was shown to have high nucleophilicity, which can be used in organic synthesis and conjugate addition to n,3-eno-nes to give 6,c-enones exclusively.
Journal ArticleDOI
Regiospecific allylation of acetals with allylsilanes catalyzed by iodotrimethylsilane. Synthesis of homoallylethers
TL;DR: In this article, allylation of acetals with allyl-silanes is catalyzed by iodotrimethylsilane to give the corresponding homoallyl ethers, with regiospecific transposition of the allyl group.
Journal ArticleDOI
2-Bromo-3-trimethylsilylpropene. An annulating agent for five-membered carbo- and heterocycles
Barry M. Trost,Brian P. Coppola +1 more
TL;DR: In this paper, the parent peak envelope for unlabeled butanedione21 was investigated and the peak ratio was predicted by taking into account 90% 13C label incorporation and the presence of natural abundance label in the unenriched positions.