期刊
TETRAHEDRON LETTERS
卷 46, 期 46, 页码 8047-8051出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.09.059
关键词
InCl3; stereoselective; 2-C-methylene glycoside; pyranobenzopyran
2-C-Acetoxymethyl glycal derivatives react with aliphatic alcohols in the presence of InCl3 (30 mol %) to furnish the corresponding 2-C-methylene glycosides in excellent yields and with exclusive alpha-selectivity except for the methyl 2-C-methylene glycosides, which are formed in similar to 2:1 anomeric ratio in favour of the alpha-anomer. The reaction of 2-C-acetoxyglycals with phenols, however, produces the corresponding chiral carbohydrate-derived pyranobenzopyran derivatives via initial Ferrier rearrangement followed by tandem cyclization in excellent yields and moderate to high stereoselectivities in favour of the corresponding 10a-R-pyrano[2,3-b][1]benzopyran derivatives. (c) 2005 Elsevier Ltd. All rights reserved.
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