期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 15, 期 -, 页码 1275-1280出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.15.125
关键词
enosides; Ferrier-rearrangement; organocatalyst; pseudo-glycosides; C-; O-; N- and S-linked glycosides
资金
- Nanyang Technological University, Singapore [RG 13/18]
A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to give a wide range of glycosides in up to 98% yields with mainly a-anomeric selectivity. The perflurophenylboronic acid successfully catalyzed a wide range of substrates (both glucals and nucleophiles) under very mild reaction conditions.
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