39203-22-0Relevant academic research and scientific papers
ORGANOCATALYTIC CARBONYL-OLEFIN AND OLEFIN-OLEFIN METATHESIS
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, (2014/02/16)
The present invention provides, inter alia, organocatalytic carbonyl-olefin metathesis process. This process involves contacting a carbonyl-containing moiety with an olefin-containing moiety in the presence of a catalyst and under conditions sufficient to form a metathesis product with the proviso that the process takes place in the absence of photochemical promotion, stoichiometric amounts of transition metals, and Brnsted and Lewis acid catalysts. The present invention also provides an organocatalytic olefin-olefin metathesis process. This process involves contacting a first olefin-containing moiety with a second olefin-containing moiety in the presence of a catalyst and under conditions sufficient to form a metathesis product with the proviso that the process takes place in the absence of stoichiometric amounts of transition metals. Products made by the processes disclosed herein are also provided.
An exclusive approach to 3,4-disubstituted cyclopentenes and alkylidene cyclopentenes via the palladium catalyzed ring opening of azabicyclic olefins with aryl halides
Joseph, Nayana,Rajan, Rani,John, Jubi,Devika,Chand, S. Sarath,Suresh,Pihko, Petri M.,Radhakrishnan
, p. 7751 - 7757 (2013/07/05)
A simple and efficient method for the stereoselective ring opening of bicyclic hydrazines with various aryl halides under palladium catalysis has been elaborated. The reactions afforded trans-3,4-disubstituted cyclopentenes or alkylidene cyclopentenes in good to excellent yields. By taking advantage of multiple points of functionalization in the synthesized trans-3-phenyl-4- hydrazino-cyclopentene, we have synthesized the antidepressant Cypenamine (trans-2-phenylcyclopentylamine).
Organocatalytic carbonyl-olefin metathesis
Griffith, Allison K.,Vanos, Christine M.,Lambert, Tristan H.
, p. 18581 - 18584 (2013/01/15)
The development of a catalytic carbonyl-olefin metathesis strategy is reported, in the context of the ring-opening metathesis of cyclopropenes with aldehydes using a simple hydrazine catalyst. The key to this reaction is a conceptual blueprint for metathesis chemistry that forgoes the traditional reliance on [2 + 2] cycloaddition modes in favor of a [3 + 2] paradigm.
Cobalt-catalyzed hydrohydrazination of dienes and enynes: Access to allylic and propargylic hydrazides
Waser, Jerome,Gonzalez-Gomez, Jose C.,Nambu, Hisanori,Huber, Pascal,Carreira, Erick M.
, p. 4249 - 4252 (2007/10/03)
(Chemical Equation Presented) The cobalt-catalyzed hydrohydrazination reaction of dienes and enynes is presented. Allylic and propargylic hydrazines were obtained in synthetically useful yields (allylic amines, 60-90%; propargylic amines, 47-83%) and good chemo- and regioselectivity.
Enantioselective desymmetrization of meso bicyclic hydrazines: A novel approach to the asymmetric synthesis of polysubstituted amino cyclopentanic cores
Perez Luna,Ceschi,Bonin,Micouin,Husson,Gougeon,Estenne-Bouhtou,Marabout,Sevrin,George
, p. 3522 - 3524 (2007/10/03)
Catalytic asymmetric hydroboration can be successfully applied to meso bicyclic hydrazines. The resulting alcohols are of great synthetic interest and can lead in a straightforward manner to cyclopentanic diamino alcohols with good enantiomeric purity.
Reductive Cleavage of the Nitrogen-Nitrogen Bond in Hydrazine Derivatives
Mellor, John M.,Smith, Neil M.
, p. 2927 - 2931 (2007/10/02)
The reductions of the 1,2-disubstituted hydrazines (4) - (7) having the activating groups toluene-p-sulphonyl, acetyl, ethoxycarbonyl, and trifluoroacetyl respectively have been studied with zinc in acetic acid, aluminium amalgam, sodium in liquid ammonia, sodium in ethanol, and Raney nickel.Satisfactory conditions have been defined for the reductive cleavage of each of these substituted hydrazines (4) -(7).The Diels-Alder adduct (12) of cyclopentadiene and diethyl azodicarboxylate has been oxidised, by m-chloroperoxybenzoic acid to give the epoxide (20), by osmium tetraoxide to give the diol (21), and via hydroboration to give the alcohol (22).Using sodium in liquid ammonia these hydrazine derivatives (20)-(22) and others have been reduced by cleavage of the nitrogen-nitrogen bond to give derivatives of oxygenated cyclic diamines.
