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Intramolecular Diels–Alder Reaction of Vinylsulfonic Acid Esters
Author(s) -
Bovenschulte Eva,
Metz Peter,
Henkel Gerald
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198902021
Subject(s) - intramolecular force , mndo , diels–alder reaction , chemistry , organic chemistry , medicinal chemistry , computational chemistry , catalysis , molecule
The highly diastereoselective intramolecular Diels–Alder reaction of the vinylsulfonate esters of the hydroxyalkylfurans 1 (R = Me, Et, i Pr) to give the sultones 2 occurs at room temperature. MNDO and MMPMI calculations indicate a thermodynamic control of the relative configurations of 2 .