A CONVENIENT ROUTE TO SUBSTITUTED TETRAHYDROFURAN-3-ONES - CONDENSATIONS OF ALPHA-BROMO KETONES WITH AROMATIC-ALDEHYDES

Authors
DONG Y CLEARY TP TODARO LJ
Citation
Y. Dong et al., A CONVENIENT ROUTE TO SUBSTITUTED TETRAHYDROFURAN-3-ONES - CONDENSATIONS OF ALPHA-BROMO KETONES WITH AROMATIC-ALDEHYDES, Tetrahedron letters, 35(50), 1994, pp. 9367-9370
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
50
Year of publication
1994
Pages
9367 - 9370
Database
ISI
SICI code
0040-4039(1994)35:50<9367:ACRTST>2.0.ZU;2-1
Abstract
In the presence of K2CO3, alpha-bromo ketones react with aromatic alde hydes in methanol to produce substituted tetrahydrofuran-3-ones 3a-g i n good yields (55% to 83%). The reaction proceeds with initial formati on of an alpha-ketoepoxide, followed by a tandem aldol reaction, cycli zation and dehydration.