A TITANIUM (IV) MEDIATED ONE-POT DOUBLE CONDENSATION SYNTHESIS OF 5,6-DIHYDRO-4H-PYRAN-4-ONES

Authors
MORRIS J WISHKA DG LUKE GP JUDGE TM GAMMILL RB
Citation
J. Morris et al., A TITANIUM (IV) MEDIATED ONE-POT DOUBLE CONDENSATION SYNTHESIS OF 5,6-DIHYDRO-4H-PYRAN-4-ONES, Tetrahedron, 53(32), 1997, pp. 11211-11222
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
32
Year of publication
1997
Pages
11211 - 11222
Database
ISI
SICI code
0040-4020(1997)53:32<11211:AT(MOD>2.0.ZU;2-0
Abstract
An alternative method for the synthesis of 2-amino-5,6-dihydro-4H-pyra n-4-ones and 5,6-dihydro-4H-pyran-4-ones is described. This preparatio n makes use of the condensation of titanium enolates derived from beta -hydroxy ketones with phosgene iminium chloride or trimethylorthoforma te, respectively. The in situ formation of the necessary titanium comp lex from an aldol condensation using simple ketone and aldehyde precur sors makes for a one-pot double condensation synthesis of the desired dihydropyrones. (C) 1997 Elsevier Science Ltd.