Cyclopentane synthesis via free radical mediated addition of functionalized alkenes to substituted vinyl cyclopropanes
作者:Ken S. Feldman、Anthony L. Romanelli、Robert E. Ruckle、Raymond F. Miller
DOI:10.1021/ja00218a050
日期:1988.5
Nouvelle strategie de synthese de cyclopentanes fonctionnalises grâce a l'addition catalysee par un radical phenylthiyle d'alcenes substitues sur des cyclopropanes vinyliques substitues
Nouvelle strategie de synthese de cyclopentanes fonctionnalises grâce a l'addition catalysee par un Radical phenylthiyle d'alcenes substitues sur des cyclopropanesvinyliques substitues
Synthesis of cyclopropyl and cyclopropenyl ethers
作者:R.A. Olofson、Kenneth D. Lotts、Gary N. Barber
DOI:10.1016/s0040-4039(00)93108-3
日期:1976.10
Vinylcyclopentane synthesis via phenylthio radical catalyzed alkenylation of vinylcyclopropanes: preparative and mechanistic studies
作者:Ken S. Feldman、Anthony L. Romanelli、Robert E. Ruckle、Ginette Jean
DOI:10.1021/jo00027a020
日期:1992.1
1-Vinylcyclopropanes bearing ether or ester substituents at C(2) of the cyclopropyl ring or alkyl groups at other ring (or alkenyl) positions were subjected to PhS. catalyzed olefination with ester- or oxygen-functionalized alkenes. In some instances, variations in reaction conditions (low temperature, Lewis acids) led to levels of stereoselectivity unprecedented in such simple, unbiased substrates. In general, the stereochemical outcome of these transformations can be rationalized by citing existing models for selectivity upon cyclization of substituted 5-hexenyl radicals. However, in a few specific instances, results obtained with alkylated vinylcyclopropyl substrates are not consistent with some of the predictions of these models.
De Meijere; Schulz; Kostikov, Synthesis, 1991, # 7, p. 547 - 560