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NCUEIR > College of Science > Department of Chemistry > Periodical Articles > Item 987654321/15027

Please use this identifier to cite or link to this item: http://ir.ncue.edu.tw/ir/handle/987654321/15027

Title:	Stereoselective Synthesis of Dioxabicycles from 1-C-allyl-2-O-benzyl-glycosides — An Intramolecular Cyclization between 2-O-benzyl Oxygen and the Allyl Double Bond
Authors:	Wu, An-Tai;Yi, Tian;Shao, Huawu;Wu, Shih-Hsiung;Zou, Wei
Contributors:	化學系
Date:	2006-12
Issue Date:	2013-01-07T01:47:36Z
Publisher:	Canadian Science Publishing
Abstract:	Addition of a proton to the double bond of 1-C-allyl-O-benzylglycosides gave a 2′-carbonium ion, which in turn reacted intramolecularly, in a regio- and diastereo-selective manner, with the nucleophilic oxygen of the 2-O-benzyl group to form an oxonium intermediate. Subsequent cleavage of the benzyl CO bond led to dioxabicycles in moderate yields. Surprisingly, opposite diastereoselectivities were observed from 1-C-allylglycofuranosides and 1-C-allylglycopyranosides, which produced 2,2′-trans- and 2,2′-cis-dioxabicycles, respectively.Key words: C-glycoside, olefin, cyclization, oxocarbonium, dioxabicycles.
Relation:	Can. J. Chem., 84(4): 597-602
Appears in Collections:	[Department of Chemistry] Periodical Articles

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