Desulfonylation with Mg−MeOH−NiBr₂: An Expedient Reagent System for the Synthesis of 2-Amino-2,3-dideoxy Furanosides

A catalytic amount of NiBr2 with Mg−MeOH increases the efficiency of reductive desulfonylation of the β-sulfonylated aminosugars. The Mg−MeOH−NiBr2 system has been utilized in the synthesis of 2-amino-2,3-dideoxypentofuranosides and 2-amino-2,3-dideoxyhexofuranosides. The yield of the desulfonylation improved dramatically from 0% with the known reagents to 44−75% with Mg−MeOH−NiBr2

Desulfonylation with Mg−MeOH−NiBr₂: An Expedient Reagent System for the Synthesis of 2-Amino-2,3-dideoxy Furanosides

A catalytic amount of NiBr2 with Mg−MeOH increases the efficiency of reductive desulfonylation of the β-sulfonylated aminosugars. The Mg−MeOH−NiBr2 system has been utilized in the synthesis of 2-amino-2,3-dideoxypentofuranosides and 2-amino-2,3-dideoxyhexofuranosides. The yield of the desulfonylation improved dramatically from 0% with the known reagents to 44−75% with Mg−MeOH−NiBr2

Desulfonylation with Mg−MeOH−NiBr₂: An Expedient Reagent System for the Synthesis of 2-Amino-2,3-dideoxy Furanosides

A catalytic amount of NiBr2 with Mg−MeOH increases the efficiency of reductive desulfonylation of the β-sulfonylated aminosugars. The Mg−MeOH−NiBr2 system has been utilized in the synthesis of 2-amino-2,3-dideoxypentofuranosides and 2-amino-2,3-dideoxyhexofuranosides. The yield of the desulfonylation improved dramatically from 0% with the known reagents to 44−75% with Mg−MeOH−NiBr2

Desulfonylation with Mg−MeOH−NiBr₂: An Expedient Reagent System for the Synthesis of 2-Amino-2,3-dideoxy Furanosides

A catalytic amount of NiBr2 with Mg−MeOH increases the efficiency of reductive desulfonylation of the β-sulfonylated aminosugars. The Mg−MeOH−NiBr2 system has been utilized in the synthesis of 2-amino-2,3-dideoxypentofuranosides and 2-amino-2,3-dideoxyhexofuranosides. The yield of the desulfonylation improved dramatically from 0% with the known reagents to 44−75% with Mg−MeOH−NiBr2

Desulfonylation with Mg−MeOH−NiBr₂: An Expedient Reagent System for the Synthesis of 2-Amino-2,3-dideoxy Furanosides

A catalytic amount of NiBr2 with Mg−MeOH increases the efficiency of reductive desulfonylation of the β-sulfonylated aminosugars. The Mg−MeOH−NiBr2 system has been utilized in the synthesis of 2-amino-2,3-dideoxypentofuranosides and 2-amino-2,3-dideoxyhexofuranosides. The yield of the desulfonylation improved dramatically from 0% with the known reagents to 44−75% with Mg−MeOH−NiBr2

Desulfonylation with Mg−MeOH−NiBr₂: An Expedient Reagent System for the Synthesis of 2-Amino-2,3-dideoxy Furanosides

A catalytic amount of NiBr2 with Mg−MeOH increases the efficiency of reductive desulfonylation of the β-sulfonylated aminosugars. The Mg−MeOH−NiBr2 system has been utilized in the synthesis of 2-amino-2,3-dideoxypentofuranosides and 2-amino-2,3-dideoxyhexofuranosides. The yield of the desulfonylation improved dramatically from 0% with the known reagents to 44−75% with Mg−MeOH−NiBr2

Desulfonylation with Mg−MeOH−NiBr₂: An Expedient Reagent System for the Synthesis of 2-Amino-2,3-dideoxy Furanosides

A catalytic amount of NiBr2 with Mg−MeOH increases the efficiency of reductive desulfonylation of the β-sulfonylated aminosugars. The Mg−MeOH−NiBr2 system has been utilized in the synthesis of 2-amino-2,3-dideoxypentofuranosides and 2-amino-2,3-dideoxyhexofuranosides. The yield of the desulfonylation improved dramatically from 0% with the known reagents to 44−75% with Mg−MeOH−NiBr2

Base Induced Chiral Substituted Furans and Imidazoles from Carbohydrate-Derived 2‑Haloenones

Chiral substituted furans and imidazoles are key intermediates to access biologically important molecules. We describe herein a catalyst/ligand free cascade Michael-type addition/intramolecular cyclization/carbohydrate-ring opening of 2-haloenones with 1,3-dicarbonyl compounds or amidines utilizing K₂CO₃/DMSO at ambient temperature that provides a straightforward approach to a variety of optically active (poly)­hydroxy furans and imidazoles containing multiple stereocenters with good yield and excellent regioselectivity. The furan intermediates provide efficient access to synthetically valuable substituted α-benzyloxyvinyl ketones. The NMR spectrum of the substituted 2-methylfurans shows an unusual long-range (⁵<i>J</i>_H–H) ¹H–¹H COSY cross-peak between C₂–CH₃ and C₄–H signals

Diastereoselective Michael Initiated Ring Closure on Vinyl Sulfone-Modified Carbohydrates: A Stereospecific and General Route to α-Substituted Cyclopropanes

Suitably designed vinyl sulfone-modified furanosides act as substrates for Michael initiated ring closure reactions yielding cyclopropanated carbohydrates. The strategy is general in nature and gives access to cyclopropanes with predefined chiralities on three consecutive carbons with varying substitutions at the α-position

Diastereoselective Michael Initiated Ring Closure on Vinyl Sulfone-Modified Carbohydrates: A Stereospecific and General Route to α-Substituted Cyclopropanes

Suitably designed vinyl sulfone-modified furanosides act as substrates for Michael initiated ring closure reactions yielding cyclopropanated carbohydrates. The strategy is general in nature and gives access to cyclopropanes with predefined chiralities on three consecutive carbons with varying substitutions at the α-position