2-and 3-haloalkoxy Fischer carbene complexes of chromium as synthons for either hydroxycyclopropanation or oxaspirocyclopropanation of alkenes

Authors
Barluenga, J Lopez, S Trabanco, AA Florez, J
Citation
J. Barluenga et al., 2-and 3-haloalkoxy Fischer carbene complexes of chromium as synthons for either hydroxycyclopropanation or oxaspirocyclopropanation of alkenes, CHEM-EUR J, 7(21), 2001, pp. 4723-4729
Citations number
55
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY-A EUROPEAN JOURNAL
ISSN journal
09476539 → ACNP
Volume
7
Issue
21
Year of publication
2001
Pages
4723 - 4729
Database
ISI
SICI code
0947-6539(20011105)7:21<4723:23FCCO>2.0.ZU;2-6
Abstract
The thermal reaction of 2-haloethoxy- and 3-chloropropoxy(alkenyl)carbene c omplexes of chromium with electronically neutral alkenes furnished diastere oselectively the corresponding 1-haloalkoxy-1-vinylcyclopropanes that, subj ected to subsequent halogen-lithium exchange reactions, provided vinyleyclo propanols or compounds containing the spiro[cyclopropane-tetrahydrofuran/te trahydropyran] structure, depending on the nature of both the halogen atom and the lithiating reagent. The hydroxycyclopropanation reaction can be eff iciently achieved in a one-pot fashion.