A BETA-LACTONE-BASED ROUTE TO CYCLOPENTANES VIA INTRAMOLECULAR ALLYLSILANE ADDITIONS - AN UNEXPECTED FRIEDEL-CRAFTS ALKYLATION

Authors
ZHAO CX ROMO D
Citation
Cx. Zhao et D. Romo, A BETA-LACTONE-BASED ROUTE TO CYCLOPENTANES VIA INTRAMOLECULAR ALLYLSILANE ADDITIONS - AN UNEXPECTED FRIEDEL-CRAFTS ALKYLATION, Tetrahedron letters, 38(37), 1997, pp. 6537-6540
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
37
Year of publication
1997
Pages
6537 - 6540
Database
ISI
SICI code
0040-4039(1997)38:37<6537:ABRTCV>2.0.ZU;2-#
Abstract
Lewis acid promoted intramolecular additions of allylsilanes to beta-l actones proceed smoothly to give variously substituted cyclopentanes. A proposed transition state assembly for this reaction guided our effo rts to improve the stereoselectivity. A novel Friedel-Crafts alkylatio n of beta-lactones is also described. (C) 1997 Elsevier Science Ltd.