Tetrahedron: Asymmetry

Expedient conversion of d-glucose into 1, 5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise …

M Brehm, VH Göckel, P Jarglis, FW Lichtenthaler

Index: Brehm, Manfred; Goeckel, Volker H.; Jarglis, Pan; Lichtenthaler, Frieder W. Tetrahedron Asymmetry, 2008 , vol. 19, # 3 p. 358 - 373

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Citation Number: 18

Abstract

High-yielding protocols are described to convert d-glucose—via hydroxylaminolysis of its hydroxyglucal esters, followed by deoximination and β-elimination of acid—into dihydropyranone building blocks with a single stereogenic center. Their versatility as enantiopure six-carbon scaffolds is highlighted by excellent regio-and stereocontrol in a variety of addition reactions and by their straightforward use as building blocks for the ...