900779-69-3Relevant academic research and scientific papers
Iron-catalyzed cyclopropanation with trifluoroethylamine hydrochloride and olefins in aqueous media: In situ generation of trifluoromethyl diazomethane
Morandi, Bill,Carreira, Erick M.
, p. 938 - 941 (2010)
Let's avoid the risk! The title transformation has been developed for the synthesis of trifluoromethyl-substituted cyclopropane derivatives (see scheme). It avoids the preparation of trifluoromethyl diazomethane and merges a number of areas: water as a reaction medium, iron catalysis, and access to reactive intermediates under operationally safe conditions. Chemical equation presented
Synthesis of trans-2-(trifluoromethyl)cyclopropanes via suzuki reactions with an N-methyliminodiacetic acid boronate
Duncton, Matthew A. J.,Singh, Rajinder
, p. 4284 - 4287 (2013)
trans-2-(Trifluoromethyl)cyclopropylboronic acid N-methyliminodiacetic acid (MIDA) ester 5 was synthesized as a pure diastereomer from vinylboronic acid MIDA ester and (trifluoromethyl)diazomethane in a single step. An X-ray study confirmed the trans-stereochemistry around the cyclopropyl ring. Use of 5 in Suzuki reactions, with a variety of aryl or heteroaryl coupling partners, provided trans-2-(trifluoromethyl)cyclopropyl products in moderate to excellent yields (17-90%).
Highly enantioselective synthesis of trifluoromethyl cyclopropanes by using Ru(ii)-Pheox catalysts
Kotozaki, Manato,Chanthamath, Soda,Fujii, Takuji,Shibatomi, Kazutaka,Iwasa, Seiji
, p. 5110 - 5113 (2018/05/26)
An asymmetric synthesis of various trifluoromethyl cyclopropanes from olefins, such as vinyl ferrocene, vinyl ethers, vinyl amines, vinyl carbamates and dienes, was achieved by using Ru(ii)-Pheox catalysts. This catalytic system can function at a low catalyst loading (3 mol%) compared with those reported previously, and the desired cyclopropane products are obtained in high yields with excellent diastereoselectivity (up to >99:1) and enantioselectivity (up to 97% ee).
Highly Diastereo- and Enantioselective Synthesis of Trifluoromethyl-Substituted Cyclopropanes via Myoglobin-Catalyzed Transfer of Trifluoromethylcarbene
Tinoco, Antonio,Steck, Viktoria,Tyagi, Vikas,Fasan, Rudi
supporting information, p. 5293 - 5296 (2017/04/27)
We report an efficient strategy for the asymmetric synthesis of trifluoromethyl-substituted cyclopropanes by means of myoglobin-catalyzed olefin cyclopropanation reactions in the presence of 2-diazo-1,1,1-trifluoroethane (CF3CHN2) as
A Trifluoromethylcarbene Source
Duan, Yaya,Lin, Jin-Hong,Xiao, Ji-Chang,Gu, Yu-Cheng
supporting information, p. 2471 - 2474 (2016/06/09)
The trifluoromethylcarbene (:CHCF3) was found to be conveniently generated from (2,2,2-trifluoroethyl)diphenyl-sulfonium triflate (Ph2S+CH2CF3 -OTf), which was successfully applied in Fe-catalyzed cyclopropanation of olefins, giving the corresponding trifluoromethylated cyclopropanes in high yields.
CYCLOPROPYL MIDA BORONATE
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Page/Page column 52, (2012/06/16)
This disclosure concerns a protected cyclopropylboronic acid comprising a substituted cyclopropyl group and a boronic ester group having a protecting group. The protecting group is an N-methyliminodiacetic acid (MIDA) group or MIDA-based group.
Enantioselective cobalt-catalyzed preparation of trifluoromethyl- substituted cyclopropanes
Morandi, Bill,Mariampillai, Brian,Carreira, Erick M.
supporting information; experimental part, p. 1101 - 1104 (2011/04/21)
Easy access on water: A cobalt-catalyzed asymmetric preparation of trifluoromethylcyclopropanes has been developed that yields high enantioselectivities with a broad range of styrene substrates (see scheme). The reaction presents a new access to enantioen
Asymmetric synthesis of trifluoromethylphenyl cyclopropanes catalyzed by chiral metalloporphyrins
Le Maux, Paul,Juillard, Sandrine,Simonneaux, Gerard
, p. 1701 - 1704 (2007/10/03)
The asymmetric addition of 2,2,2-trifluorodiazoethane to styrene derivatives to give optically active trifluoromethylphenyl cyclopropanes (ee values up to 69%) was carried out by using chiral iron and ruthenium porphyrins as homogeneous and heterogeneous catalysts. Georg Thieme Verlag Stuttgart.
