SYNTHESIS AND REACTIONS OF 1,2-DISUBSTITUTED METHYLENECYCLOPROPANES PREPARED VIA INTRAMOLECULAR CYCLOPROPANATION OF ALLENIC DIAZOACETATES

Authors
LAUTENS M MEYER C VANOEVEREN A
Citation
M. Lautens et al., SYNTHESIS AND REACTIONS OF 1,2-DISUBSTITUTED METHYLENECYCLOPROPANES PREPARED VIA INTRAMOLECULAR CYCLOPROPANATION OF ALLENIC DIAZOACETATES, Tetrahedron letters, 38(22), 1997, pp. 3833-3836
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
22
Year of publication
1997
Pages
3833 - 3836
Database
ISI
SICI code
0040-4039(1997)38:22<3833:SARO1M>2.0.ZU;2-Q
Abstract
Diazoacetates derived from alpha- or beta- allenic alcohols, prepared using the glyoxylic acid chloride p-toluenesulfonylhydrazone method, u ndergo regioselective intramolecular cyclopropanation in the presence of a copper (II) catalyst in refluxing toluene, leading to synthetical ly useful di- or trisubstituted methylenecyclopropyl lactones. The dia stereoselectivity of the process has been studied. (C) 1997 Elsevier S cience Ltd.