TRIMETHYLSILYLKETENE DIALKYLACETALS IN ORGANIC-SYNTHESIS - REACTIONS WITH ALKYLDIAZOACETATES

Authors
ZAITSEVA GS NOVIKOVA OP GRIGORIEV EV KISIN AV AVTOMONOV EV LORBERTH J
Citation
Gs. Zaitseva et al., TRIMETHYLSILYLKETENE DIALKYLACETALS IN ORGANIC-SYNTHESIS - REACTIONS WITH ALKYLDIAZOACETATES, Journal of organometallic chemistry, 525(1-2), 1996, pp. 175-181
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Journal of organometallic chemistry → ACNP
ISSN journal
0022328X
Volume
525
Issue
1-2
Year of publication
1996
Pages
175 - 181
Database
ISI
SICI code
0022-328X(1996)525:1-2<175:TDIO-R>2.0.ZU;2-O
Abstract
The reaction of trimethylsilylketene dialkylacetals with alkyldiazoace tates in the presence of Cu(acac)(2) or Rh-2(OAc)(4) results in the fo rmation of alkoxy-3-trimethylsilylcyclopropane-1-carboxylates 3-8. The cycloaddition proceeds stereoselectively, giving exclusively one of t wo possible diastereomers. Compounds 4 and 6 are transformed by reacti on with LiAIH(4), to cyclopropylmethanols 9 and 10 in high yields. All compounds have been characterized by elemental analyses, H-1, C-13 NM R and IR spectroscopy.