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Aromatic Claisen rearrangements in carbohydrates: Stereocontrol of rearrangement rates in unsaturated sugar substrates
Kalapattukuppuswamy Kuppuswamy B. Balasubramanian
Published in
Issue: 7
Pages: 1399 - 1401
A remarkable difference is observed in the rates of [3,3]-sigmatropic rearrangement of aryl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides 1 and 2; the slower reactivity of the α-isomers is consistent with AM1 calculated transition state energetics of model systems.
About the journal
JournalJournal of the Chemical Society, Perkin Transactions 2
Open AccessNo