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Diastereoselective Self‐Condensation of Dihydroxyfumaric Acid in Water: Potential Route to Sugars
Author(s) -
Naidu Sagi Vasudeva,
Karri Phaneendrasai,
Hu Fang,
Krishnamurthy Ramanarayanan
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201102045
Subject(s) - synthon , nucleophile , electrophile , diastereomer , salt (chemistry) , chemistry , condensation , organic chemistry , transformation (genetics) , metal , catalysis , biochemistry , physics , thermodynamics , gene
Jack of all trades : Water‐soluble salts of DHF underwent self‐condensation to afford the threo diastereomer of pentulosonic acid, through differing reaction pathways contingent on the metal salt used (see scheme). This transformation exemplifies the diverging roles of DHF as a nucleophile (a synthon for α‐hydroxyacetyl anion) and an electrophile (an α‐carboxyglycolaldehyde equivalent).