38323-08-9Relevant academic research and scientific papers
Design, preparation, X-ray crystal structure, and reactivity of o-alkoxyphenyliodonium bis(methoxycarbonyl)methanide, a highly soluble carbene precursor
Zhu, Chenjie,Yoshimura, Akira,Ji, Lei,Wei, Yunyang,Nemykin, Victor N.,Zhdankin, Viktor V.
supporting information; experimental part, p. 3170 - 3173 (2012/08/07)
The preparation, X-ray structure, and reactivity of new, highly soluble, and reactive iodonium ylides derived from malonate methyl ester and bearing an ortho substituent on the phenyl ring are reported. These new reagents show higher reactivity than common phenyliodonium ylides in the Rh-catalyzed cyclopropanation, C-H insertion, and transylidation reactions under homogeneous conditions.
Rhodium-catalyzed cyclopropanation of alkenes with dimethyl diazomalonate
Gonzalez-Bobes, Francisco,Fenster, Michael D. B.,Kiau, Susanne,Kolla, Laxma,Kolotuchin, Sergei,Soumeillant, Maxime
supporting information; experimental part, p. 813 - 816 (2009/04/21)
The outstanding ability of dirhodium α,α,α′, α′-tetramethyl-1,3-benzenedipropanoate [Rh2(esp) 2; esp=α,α,α′,α′-tetramethyl-1,3- benzene-dipropanoate] to catalyze the cyclopropanation of a wide range of alkenes with malonate-derived carbenoids under mild reaction conditions is reported in this communication. The experimental protocol is remarkably simple, uses readily accessible and stable dimethyl diazomalonate with very low catalyst loading. More importantly, the alkene is employed as a limiting reagent.
Examination of homo-[3 + 2]-dipolar cycloaddition: Mechanistic insight into regio-and diastereoselectivity
Karadeolian, Avedis,Kerr, Michael A.
, p. 10251 - 10253 (2008/03/28)
(Chemical Equation Presented) The reaction of 2,3-disubstituted-1,1- cyclopropanediesters with nitrones under Lewis acid conditions produces tetrahydro-1,2-oxazines in which the cis/trans relationship of the cyclopropanes is not conserved. Reacting nitrones with 2,3-cis-disubstituted cyclopropanes lead to 5,6-trans-oxazines, and 2,3-trans-disubstituted cyclopropanes lead to 5,6-cis-oxazines. This observed stereochemical inversion provides evidence for a stepwise annulation mechanism in the preparation of tetrahydro-1,2-oxazines.
