LEWIS-ACID INDUCED ALKOXYALKYLATION OF ALLYLSILANES WITH ACETALS (THESAKURAI REACTION) - REGIOCHEMICAL AND STEREOCHEMICAL ASPECTS

Authors
POLLA M FREJD T
Citation
M. Polla et T. Frejd, LEWIS-ACID INDUCED ALKOXYALKYLATION OF ALLYLSILANES WITH ACETALS (THESAKURAI REACTION) - REGIOCHEMICAL AND STEREOCHEMICAL ASPECTS, Acta chemica Scandinavica, 47(7), 1993, pp. 716-720
Citations number
17
Categorie Soggetti
Chemistry,Biology
Journal title
Acta chemica Scandinavica → ACNP
ISSN journal
0904213X
Volume
47
Issue
7
Year of publication
1993
Pages
716 - 720
Database
ISI
SICI code
0904-213X(1993)47:7<716:LIAOAW>2.0.ZU;2-X
Abstract
The electrophile generated from 1,1-diethoxyethane and TMSOTf reacts w ith allylic silanes 1a,b to give the expected gamma-substitution produ cts. However, when the gamma-position is sterically hindered as in 1c substitution occurs at the alpha-position, presumably due to prior pro todesilylation followed by electrophilic alkylation of the resulting o lefin. This protodesilylation pathway may also explain similar results reported by other groups.