82126-26-9Relevant academic research and scientific papers
Stereoselective cis-Vinylcyclopropanation via a Gold(I)-Catalyzed Retro-Buchner Reaction under Mild Conditions
Herlé, Bart,Holstein, Philipp M.,Echavarren, Antonio M.
, p. 3668 - 3675 (2017/06/09)
A highly stereoselective gold(I)-catalyzed cis-vinylcyclopropanation of alkenes has been developed. Allylic gold carbenes, generated via a retro-Buchner reaction of 7-alkenyl-1,3,5-cycloheptatrienes, react with alkenes to form vinylcyclopropanes. The gold(I)-catalyzed retro-Buchner reaction of these substrates proceeds by simple heating at a temperature much lower than that required for the reaction of 7-aryl-1,3,5-cycloheptatrienes (75 °C vs 120 °C). A newly developed Julia-Kocienski reagent enables the synthesis of the required cycloheptatriene derivatives in one step from readily available aldehydes or ketones. On the basis of mechanistic investigations, a stereochemical model for the cis selectivity was proposed. An unprecedented gold-catalyzed isomerization of cis- to trans-cyclopropanes has also been discovered and studied by DFT calculations.
Gold(I)-Catalyzed Synthesis of Indenes and Cyclopentadienes: Access to (±)-Laurokamurene B and the Skeletons of the Cycloaurenones and Dysiherbols
Yin, Xiang,Mato, Mauro,Echavarren, Antonio M.
supporting information, p. 14591 - 14595 (2017/10/18)
The formal (3+2) cycloaddition between terminal allenes and aryl or styryl gold(I) carbenes generated by a retro-Buchner reaction of 7-substituted 1,3,5-cycloheptatrienes led to indenes and cyclopentadienes, respectively. These cycloaddition processes have been applied to the construction of the carbon skeleton of the cycloaurenones and the dysiherbols as well as to the total synthesis of (±)-laurokamurene B.
Cyclopropanation with gold(I) carbenes by retro-Buchner reaction from cycloheptatrienes
Solorio-Alvarado, César R.,Wang, Yahui,Echavarren, Antonio M.
supporting information; experimental part, p. 11952 - 11955 (2011/10/04)
Cationic gold(I) promotes the retro-Buchner reaction of 7-substituted 1,3,5-cycloheptatrienes, leading to gold(I) carbenes that cyclopropanate alkenes.
PHOTOREACTIONS OF 2,3-DIAZATETRACYCLOUNDECA-2,9-DIENES; THE RETRO-1,3-DIPOLAR CYCLOADDITIONS AND THE NITROGEN EXTRUSION REACTIONS
Kumagai, Tsutomu,Ohba, Yoshihiro,Mukai, Toshio
, p. 439 - 442 (2007/10/02)
The photochemical reactions of tetracyclic azo compounds (1a-b) giving 5a-b and 8a-b via diazoethane derivatives (6a-b) were investigated in addition to the nitrogen extrusion reactions leading to tetracyclononenes (4a-b).
