Alkylation of vinyl sulfones as a route to 2-alkylidene tetrahydrofurans

Authors
Edwards, GL Sinclair, DJ
Citation
Gl. Edwards et Dj. Sinclair, Alkylation of vinyl sulfones as a route to 2-alkylidene tetrahydrofurans, TETRAHEDR L, 40(20), 1999, pp. 3933-3934
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
20
Year of publication
1999
Pages
3933 - 3934
Database
ISI
SICI code
0040-4039(19990514)40:20<3933:AOVSAA>2.0.ZU;2-Q
Abstract
Deprotonation of the vinyl sulfone (2) with n-butyllithium and treatment of the resulting organolithium intermediate with an alkyl halide in the prese nce of hexamethylphosphoramide (HMPA) gives monoalkylated adducts in 14 to 61% yields. In general, excellent regioselectivity for alkylation alpha to the sulfone is observed. (C) 1999 Elsevier Science Ltd. All rights reserved .