Stereoselective synthesis of 3-hydroxy-2-sulfonyltetrahydrofurans from beta-(triethylsilyloxy) aldehydes and p-tolylsulfonyldiazomethane

A new method for the stereoselective syntheses of 2-sulfonyltetrahydrofurans from beta-(triethylsilyloxy)aldehydes and p-tolyl-sulfonyldiazomethane in the presence of BF3. OEt2 as Lewis acid is reported. The versatility of the sulfonyl functional group allows further functionalization alpha to the s...

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 24; pp. 5227 - 5232
Main Authors Angle, Shaw, SZ
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 11.06.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NATURAL-PRODUCTS
SULFONES
C-GLYCOSIDES
SUBSTITUTION-REACTIONS
TIN(II) CHLORIDE
OXOCARBENIUM IONS
ETHYL DIAZOACETATE
NUCLEOPHILES
tetrahydrofurans
stereoselection
diazo compounds
2-BENZENESULFONYL CYCLIC ETHERS
sulfone
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Summary:A new method for the stereoselective syntheses of 2-sulfonyltetrahydrofurans from beta-(triethylsilyloxy)aldehydes and p-tolyl-sulfonyldiazomethane in the presence of BF3. OEt2 as Lewis acid is reported. The versatility of the sulfonyl functional group allows further functionalization alpha to the sulfonyl group. For example, treatment of 2-sulfonlytetrahydrofuran 2b with BF3. OEt2 and allyl silane afforded alkylative desulfonylation product in 85% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/S0040-4020(01)00365-9