15833-44-0Relevant academic research and scientific papers
Photoredox catalysed allylic trifluoromethylation via ring opening of vinyl cyclopropanes using Langlois reagent
Chandu, Palasetty,Ghosh, Krishna Gopal,Das, Debabrata,Sureshkumar, Devarajulu
, (2019)
Trifluoromethylation of vinylcyclopropanes (VCPs) has been developed under mild reaction conditions to synthesize allylic trifluoromethylated derivatives with high yield and E/Z selectivity using visible light photo-redox catalysis and Langlois reagent (CF3SO2Na) as a trifluoromethylation source. Further, we demonstrate a gram scale synthesis procedure for a trifluoromethylation of vinylcyclopropane.
Scope and mechanism for Lewis acid-catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes: Evidence for a stereospecific intimate ion pair pathway
Pohlhaus, Patrick D.,Sanders, Shanina D.,Parsons, Andrew T.,Li, Wei,Johnson, Jeffrey S.
, p. 8642 - 8650 (2008/12/23)
In this work, the one-step diastereoselective synthesis of cis-2,5-disubstituted tetrahydrofurans via Lewis acid catalyzed [3 + 2] cycloadditions of donor-acceptor (D-A) cyclopropanes and aldehydes is described. The scope and limitations with respect to both reaction partners are provided. A detailed examination of the mechanism has been performed, including stereochemical analysis and electronic profiling of both reactants. Experimental evidence supports an unusual stereospecific intimate ion pair mechanism wherein the aldehyde functions as a nucleophile and malonate acts as the nucleofuge. The reaction proceeds with inversion at the cyclopropane donor site and allows absolute stereochemical information to be transferred to the products with high fidelity. The mechanism facilitates the stereospecific synthesis of a range of optically active tetrahydrofuran derivatives from enantioenriched D-A cyclopropanes.
