INTRAMOLECULAR 4-CYCLOADDITIONS - ALLYLIC SULFONES AS PRECURSORS TO VINYLTHIONIUM IONS(3)

Authors
HARMATA M KAHRAMAN M
Citation
M. Harmata et M. Kahraman, INTRAMOLECULAR 4-CYCLOADDITIONS - ALLYLIC SULFONES AS PRECURSORS TO VINYLTHIONIUM IONS(3), Tetrahedron letters, 39(21), 1998, pp. 3421-3424
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
21
Year of publication
1998
Pages
3421 - 3424
Database
ISI
SICI code
0040-4039(1998)39:21<3421:I4-ASA>2.0.ZU;2-U
Abstract
Treatment of a THF solution of(E)-3 with n-BuLi followed by quenching with an electrophile generally results in regioselective alkylation al pha to the sulfone with the alkene possessing (E) stereochemistry in t he major product. High selectivity for the (E) alkylation product can be achieved in the presence of small amounts of HMPA. When those (E) a lkylation products possessing a diene moiety in the side chain are tre ated with Lewis acids, 4+3 cycloaddition products are formed in good t o excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved .