Anomeric Configuration-Directed Diastereoselective C− C Bond Formation in Vinyl Sulfone-Modified Carbohydrates: A General Route to Branched-Chain Sugars
AK Sanki, CG Suresh, UD Falgune, T Pathak - Organic Letters, 2003 - ACS Publications
AK Sanki, CG Suresh, UD Falgune, T Pathak
Organic Letters, 2003•ACS PublicationsThis is the first report on the diastereoselective addition of carbon nucleophiles to vinyl
sulfone-modified hex-2-enopyranosides and pent-2-enofuranosides. Nucleophiles add to
the C-2 position from a direction opposite to that of the disposition of the anomeric methoxy
group. This novel concept of anomeric configuration-directed stereocontrolled carbon−
carbon bond formation in vinyl sulfone-modified carbohydrates is general in nature and has
been implemented in the synthesis of new hexopyranosyl and pentofuranosyl branched …
sulfone-modified hex-2-enopyranosides and pent-2-enofuranosides. Nucleophiles add to
the C-2 position from a direction opposite to that of the disposition of the anomeric methoxy
group. This novel concept of anomeric configuration-directed stereocontrolled carbon−
carbon bond formation in vinyl sulfone-modified carbohydrates is general in nature and has
been implemented in the synthesis of new hexopyranosyl and pentofuranosyl branched …
This is the first report on the diastereoselective addition of carbon nucleophiles to vinyl sulfone-modified hex-2-enopyranosides and pent-2-enofuranosides. Nucleophiles add to the C-2 position from a direction opposite to that of the disposition of the anomeric methoxy group. This novel concept of anomeric configuration-directed stereocontrolled carbon−carbon bond formation in vinyl sulfone-modified carbohydrates is general in nature and has been implemented in the synthesis of new hexopyranosyl and pentofuranosyl branched-chain sugars and densely functionalized carbohydrates.
ACS Publications