IS A HYDROGEN-BONDED CARBENE AN INTERMEDIATE IN THE ORGANOALUMINUM-INDUCED RING-OPENING OF PYRANOSIDES

Authors
OLSSON R BERG U FREJD T
Citation
R. Olsson et al., IS A HYDROGEN-BONDED CARBENE AN INTERMEDIATE IN THE ORGANOALUMINUM-INDUCED RING-OPENING OF PYRANOSIDES, Tetrahedron letters, 38(32), 1997, pp. 5701-5704
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
32
Year of publication
1997
Pages
5701 - 5704
Database
ISI
SICI code
0040-4039(1997)38:32<5701:IAHCAI>2.0.ZU;2-G
Abstract
Semiempirical and ab initio quantum chemical computations indicate tha t the intermediate formed prior to the selectivity-determining methyl transfer step in the reaction between glycosides and trimethylaluminum is a strongly hydrogen-bonded equilibrium O ... H-C = O-H ... C, whic h is proposed to be an important selectivity promoting factor in the a lkyl transfer reaction. (C) 1997 Elsevier Science Ltd.