Protecting group and solvent control of stereo- and chemoselectivity in glucal 3-carbamate amidoglycosylation.

A highly stereoselective BF3·OEt2-promoted tandem hydroamination–glycosylation on a glycal scaffold has been developed to form 3-amino-2,3-dideoxysugars in a one-pot procedure. This efficient multicomponent reaction protocol offers simplicity and general applicability to a broad range of variations on each component.

Ready access to 3-amino-2,3-dideoxysugars via regio- and stereo-selective tandem hydroamination–glycosylation of glycals

Microwave-assisted stereoselective α-2-deoxyglycosylation of hex-1-en-3-uloses

Synthesis of new 2-phosphono-α-d-glycoside derivatives by stereoselective oxa-Michael addition to a d-galacto derived enone

Synthesis of α-2-deoxy-ulosides by Michael addition of hex-1-en-3-ones

Synthesis of α‐2‐Deoxyglycosides by Acid‐Mediated Conjugate Addition

A new method for the synthesis of α‐2‐deoxyglycosides from hex‐1‐en‐3‐uloses is reported. Several acids were surveyed for their ability to mediate the conjugate addition of cyclohexanol to a glucal derived α,β‐unsaturated ketone. Although several acids successfully afforded the α‐2‐deoxy‐3‐uloside as a single anomer, Ph3P  · HBr in benzene afforded the highest yield of product. These conditions were then applied to other alcohol nucleophiles, and it was found that nonsterically hindered alcohols readily undergo conjugate addition. Finally, the stereoselectivity of reduction of the resulting α‐2‐deoxy‐3‐uloside was determined for several hydride‐reducing agents.

Daniel Pitts

Papers

Synthesis of α‐2‐Deoxyglycosides by Acid‐Mediated Conjugate Addition

Synthesis of α-2-Deoxyglycosides by Acid-Mediated Conjugate Addition.