130165-29-6Relevant academic research and scientific papers
Development of a method for the reductive cyclization of enones by a titanium catalyst
Kablaoui, Natasha M.,Buchwald, Stephen L.
, p. 3182 - 3191 (1996)
An effective protocol in which bis(trimethylphosphine)titanocene is used to catalyze the reductive cyclization of enones to cyclopentanols via a metallacyclic intermediate has been developed. The key step in the process is the cleavage of the titanium-oxygen bond in the metallacycle by a silane to regenerate the catalyst. Mechanistic aspects of the reaction are discussed and the diastereoselectivity of the transformation is studied using both achiral and chiral substrates. The scope and limitations of the procedure are described. An in situ protocol for the generation of the air- and moisture-sensitive catalyst has also been developed. This work demonstrates, for the first time, the viability of using an early transition metal complex to catalyze the reductive cyclization of an alkene with a heteroatom-containing functional group.An effective protocol in which bis(trimethylphosphine) titanocene is used to catalyze the reductive cyclization of enones to cyclopentanols via a metallacyclic intermediate has been developed. The key step in the process is the cleavage of the titanium-oxygen bond in the metallacycle by a silane to regenerate the catalyst. Mechanistic aspects of the reaction are discussed and the diastereoselectivity of the transformation is studied using both achiral and chiral substrates. The scope and limitations of the procedure are described. An in situ protocol for the generation of the air-and moisture-sensitive catalyst has also been developed. This work demonstrates, for the first time, the viability of using an early transition metal complex to catalyze the reductive cyclization of an alkene with a heteroatom containing functional group.
SN2′ Alkylation of cyclopropanols via homoenolates
Das, Pragna Pratic,Belmore, Ken,Cha, Jin Kun
supporting information, p. 9517 - 9520 (2012/10/30)
Reining in reactivity: Stereoselective SN2′ alkylation of cyclopropanols has been devised under the control of mixed zinc/copper reagents. This method provides convenient access to enantiopure keto homoenolates which react with electrophiles (E
