96851-44-4Relevant academic research and scientific papers
Lactone radical cyclizations and cyclization cascades mediated by SmI 2-H2O
Parmar, Dixit,Matsubara, Hiroshi,Price, Kieran,Spain, Malcolm,Procter, David J.
supporting information; experimental part, p. 12751 - 12757 (2012/09/05)
Unsaturated lactones undergo reductive radical cyclizations upon treatment with SmI2-H2O to give decorated cycloheptanes in a single highly selective operation during which up to three contiguous stereocenters are generated. Furthermore, cascade processes involving lactones bearing two alkenes, an alkene and an alkyne, or an allene and an alkene allow "one-pot" access to biologically significant molecular scaffolds with the construction of up to four contiguous stereocenters. The cyclizations proceed by the trapping of radical anions formed by electron transfer reduction of the lactone carbonyl.
Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols
Kleinbeck, Florian,Toste, F. Dean
supporting information; experimental part, p. 9178 - 9179 (2009/12/06)
(Chemical Equation Presented) The asymmetric gold(I)-catalyzed ring expansion of 1-allenylcyclopropanols is described. The method provides synthetically valuable cyclobutanones with a vinyl-substituted quaternary stereogenic center in high enantioselectivities and yields. The method shows a broad substrate scope, tolerating protected alcohols and amines, alkenes, unsaturated esters, and acetals. The reaction is easily adjustable to large-scale synthesis, leading to product formation without significant loss of selectivity or yield with only 0.5 mol% catalyst loading.
