CONTROL OF CHEMOSELECTIVITY IN DIRHODIUM(II)-CATALYZED REACTION OF 5,6-DIOXYGENATED 2-DIAZO-3-OXOHEXANOATES - C-H INSERTION REACTION VERSUSOXONIUM YLIDE FORMATION

Authors
YAKURA T UEKI A MORIOKA Y KURATA T TANAKA K IKEDA M
Citation
T. Yakura et al., CONTROL OF CHEMOSELECTIVITY IN DIRHODIUM(II)-CATALYZED REACTION OF 5,6-DIOXYGENATED 2-DIAZO-3-OXOHEXANOATES - C-H INSERTION REACTION VERSUSOXONIUM YLIDE FORMATION, Chemical and Pharmaceutical Bulletin, 46(7), 1998, pp. 1182-1183
Citations number
18
Categorie Soggetti
Chemistry Medicinal",Chemistry,"Pharmacology & Pharmacy
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
46
Issue
7
Year of publication
1998
Pages
1182 - 1183
Database
ISI
SICI code
0009-2363(1998)46:7<1182:COCIDR>2.0.ZU;2-Y
Abstract
Methyl -4-(3,3-dimethyl-2,4-dioxolan-1-yl)-3-oxobutanoate (1), upon tr eatment with Rh-2(OAc)(4) in boiling dichloromethane, gave -7-oxo-3,8- dioxabicyclo[3.2.1]octane-1-carboxylate (2) via oxonium Slide formatio n/1,2-shift. On the other hand, similar treatment of methyl (tertbutyl dimethylsilyloxy)-2-diazo-3-oxohexanoate (3a) gave methyl methylsilylo xy)-5-oxo-1-cyclopentene-1-carboxylate (4a) via the C-H insertion reac tion.