ALLYLDIMETHYLTRITYLSILANE - SYNTHESIS OF CYCLOPENTANOLS, OXETANES, AND TETRAHYDROFURANS BY REACTION WITH ELECTRON-DEFICIENT OLEFINS

Authors
GROANING MD BRENGEL GP MEYERS AI
Citation
Md. Groaning et al., ALLYLDIMETHYLTRITYLSILANE - SYNTHESIS OF CYCLOPENTANOLS, OXETANES, AND TETRAHYDROFURANS BY REACTION WITH ELECTRON-DEFICIENT OLEFINS, Journal of organic chemistry, 63(16), 1998, pp. 5517-5522
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
16
Year of publication
1998
Pages
5517 - 5522
Database
ISI
SICI code
0022-3263(1998)63:16<5517:A-SOCO>2.0.ZU;2-Y
Abstract
Allyldimethyltritylsilane (ADTS, 1) has been employed to access a vari ety of cyclopentanols via Lewis acid mediated annulation to electron d eficient olefins. The intermediate silylcyclopentanes were converted t o their respective cyclopentanols under mild, nonepimerizing oxidative conditions. In addition, ADTS undergoes efficient annulation onto ald ehydes to provide oxetanes and tetrahydrofurans. Same preliminary inve stigations of this annulation to chiral nonracemic bicyclic lactams ar e presented.