176502-43-5Relevant articles and documents
Iodobenzene-catalyzed intramolecular oxidative cyclization reactions of ss-Alkynyl β-Ketoesters
Rodriguez, Arantxa,Moran, Wesley J.
supporting information; experimental part, p. 2220 - 2223 (2011/06/24)
Chemical equations presented. Iodobenzene is shown to catalyze the 5-exo-dig cyclization of ss-alkynyl β-ketoesters under oxidative conditions that generate hypervalent iodine species in situ. The cyclopentane products contain adjacent quaternary and tertiary stereocenters which are generated with excellent diastereoselectivity.
New cobalt-catalyzed cycloisomerization of ε-acetylenic β-keto esters. Application to a powerful cyclization reactions cascade
Cruciani, Paul,Stammler, Robert,Aubert, Corinne,Malacria, Max
, p. 2699 - 2708 (2007/10/03)
The full details of investigations into the cobalt(I)-catalyzed ene type reaction of ε-acetylenic β-keto esters to form highly functionalized methylenecyelopentanes are described. The observed regio-, chemo-, and stereoselectivities support a process of cycloisomerization which controls the relative stereochemistry of two contiguous stereogenic centers. An efficient route to the basic skeleton of the phyllocladane family has been achieved via a one-pot sequence of cyclizations: ene type, [2 + 2 + 2], [4 + 2]. This new cascade created six carbon-carbon bonds and four rings in a totally stereoselective manner from an easily accessible acyclic polyunsaturated precursor.