Stereoselectivity in the Lewis Acid Mediated Reduction of Ketofuranoses | Zendy

Erwin R. van Rijssel | Zendy; Pieter van Delft | Zendy; Daan V. van Marle | Zendy; S. Bijvoets | Zendy; Gerrit Lodder | Zendy; Herman S. Overkleeft | Zendy; Gijsbert A. van der Marel | Zendy; Dmitri V. Filippov | Zendy; Jeroen D. C. Codée | Zendy

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Stereoselectivity in the Lewis Acid Mediated Reduction of Ketofuranoses

Author(s) -

Erwin R. van Rijssel,

Pieter van Delft,

Daan V. van Marle,

S. Bijvoets,

Gerrit Lodder,

Herman S. Overkleeft,

Gijsbert A. van der Marel,

Dmitri V. Filippov,

Jeroen D. C. Codée

Publication year - 2015

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.5b00419

Subject(s) - chemistry , stereoselectivity , oxocarbenium , triethylsilane , lewis acids and bases , nucleophile , stereochemistry , conformational isomerism , arabinose , xylose , organic chemistry , molecule , catalysis , fermentation

The Lewis acid mediated reduction of ribose-, arabinose-, xylose-, and lyxose-derived methyl and phenyl ketofuranoses with triethylsilane as nucleophile was found to proceed with good to excellent stereoselectivity to provide the 1,2-cis addition products. The methyl ketoses reacted in a more stereoselective manner than their phenyl counterparts. The stereochemical outcome of the reactions parallels the relative stability of the oxocarbenium ion conformers involved, as assessed by calculating the free energy surface maps of their complete conformational space. The Lewis acid mediated reduction allows for a direct synthesis of C-glycosides with predictable stereochemistry.

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