Journal
TETRAHEDRON LETTERS
Volume 50, Issue 10, Pages 1139-1142Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.12.091
Keywords
alpha-Alkylation; Asymetric synthesis; Carbohydrates; Chiral auxiliary; Stereoselective synthesis
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Allylation and benzylation at the alpha-carbon of alpha-methylated acetoacetyl (2-methyl-3-oxobutanoyl) group incorporated into the 2-OH of methyl 6-deoxy-3,4-O-(tert-butyldimethylsilyl)-alpha-D-glucopyranoside provided the respective alpha,alpha-differentially alkylated acetoacetyl derivatives, both with high diastereoselectivity. Thus-obtained doubly alkylated products possess an all-carbon quaternary stereogenic center with an absolute stereochemistry opposite to that introduced by using the 4-O-acetoacetyl regioisomer as the alkylation substrate. (C) 2008 Elsevier Ltd. All rights reserved.
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