114095-61-3Relevant articles and documents
Enantioselective Copper-Catalyzed 1,5-Cyanotrifluoromethylation of Vinylcyclopropanes
Zhang, Zi-Qi,Meng, Xiang-Yu,Sheng, Jie,Lan, Quan,Wang, Xi-Sheng
, p. 8256 - 8260 (2019)
A copper-catalyzed enantioselective 1,5-cyanotrifluoromethylation of vinylcyclopropanes has been developed using a radical relay strategy. This asymmetric reaction has demonstrated high enantioselective control, broad substrate scope, and mild conditions. Initiated by the in situ generated CF3 radical from Togni's reagent, this method offers a new solution for remote enantioselective bifunctionalization of alkenes and thus provides a straightforward way for the synthesis of chiral CF3-containing internal alkenylnitriles.
Metal-free domino Cloke-Wilson rearrangement-hydration-dimerization of cyclopropane carbaldehydes: A facile access to oxybis(2-aryltetrahydrofuran) derivatives
Banerjee, Prabal,Dey, Raghunath,Rajput, Shruti
, (2020/03/13)
In this work, we have demonstrated a metal-free transformation of cyclopropane carbaldehydes to oxybis(2-aryltetrahydrofuran) derivatives via a domino Cloke-Wilson rearrangement-hydration-dimerization sequence. Commercially inexpensive p-toluene sulfonic acid (PTSA) was used as a Br?nsted acid catalyst, and reactions were conducted in an open-flask. Detection of reaction intermediates were carried to get an insight into the reaction pathway.
Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine
Banerjee, Prabal,Kumar, Pankaj,Kumar, Rakesh
, p. 6535 - 6550 (2020/06/09)
A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.