1280738-17-1Relevant articles and documents
Synthesis of α-Difluoromethyl Aryl Ketones through a Photoredox Difluoromethylation of Enol Silanes
Arseniyadis, Stellios,Cambeiro, Xacobe C.,Selmi-Higashi, Elias,Zhang, Jinlei
supporting information, p. 4239 - 4243 (2021/06/28)
We report here an efficient and highly straightforward access to α-difluoromethylated ketones through a visible light-mediated difluoromethylation of readily available enol silanes. The method, which takes advantage of the polyvalence of Hu's reagent, N-tosyl-S-difluoromethyl-S-phenylsulfoximine, used here as a CHF2 radical precursor under catalytic photoredox conditions, is practical, scalable, and provides the corresponding α-CHF2 ketones in good to excellent yields.
Chemo- and Regioselective Ring Construction Driven by Visible-Light Photoredox Catalysis: an Access to Fluoroalkylated Oxazolidines Featuring an All-Substituted Carbon Stereocenter
Chu, Xue-Qiang,Ge, Danhua,Wang, Mao-Lin,Rao, Weidong,Loh, Teck-Peng,Shen, Zhi-Liang
supporting information, p. 4082 - 4090 (2019/08/01)
The unique advantages conferred by incorporation of all-substituted carbon stereocenters in organic molecules have gained widespread recognition. In this work, we describe a three-component cyclization to access C-2 fluoroalkylated oxazolidines by fragments assembly of readily available silyl enol ether, fluoroalkyl halide, and chiral amino alcohol in a single reaction vessel, which provides an efficient strategy for expanding the pool of pharmaceutically important heterocycles featuring an all-substituted carbon stereocenter. This process proceeds efficiently in a chemo-, regio-, and stereoselective fashion under mild reaction conditions at room temperature and exhibits broad functional group tolerance. The successful realization of this controlled heteroannulation sequence relies on distinctive perfluoroalkylation, regio- and stereoselective radical cyclization through visible-light photoredox catalysis. Moreover, a one-pot procedure directly employing ketone as substrate has also been achieved. (Figure presented.).
Catalytic [3+2] annulation of aminocyclopropanes for the enantiospecific synthesis of cyclopentylamines
De Nanteuil, Florian,Waser, Jerome
supporting information; experimental part, p. 12075 - 12079 (2012/02/14)
With nitrogen too: The first catalytic [3+2] annulation of aminocyclopropanes with enol ethers is reported (see scheme; Phth=phthaloyl). The reaction worked with easily accessible phthalimidocyclopropanes using 5 mol % of SnCl4 in nearly quantitative yields. Polysubstituted cyclopentylamines, which are often present in bioactive compounds, were obtained with high diastereoselectivity and enantiospecificity. Copyright
