Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5272778 | Tetrahedron Letters | 2009 | 4 Pages |
Abstract
Allylation and benzylation at the α-carbon of α-methylated acetoacetyl (2-methyl-3-oxobutanoyl) group incorporated into the 2-OH of methyl 6-deoxy-3,4-O-(tert-butyldimethylsilyl)-α-d-glucopyranoside provided the respective α,α-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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Yoko Akashi, Ken-ichi Takao, Kin-ichi Tadano,