173546-40-2

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 51860-45-8 3-hydroxypropyltriphenylphosphonium bromide 
• 184360-95-0 (E)-4-((p-trifluoromethyl)phenyl)but-3-enoic acid 
• 187950-48-7 methyl (E)-4-[4-(trifluoromethyl)phenyl]but-3-enoate 
• 173546-22-0 4-(4-trifluoromethylphenyl)but-3-yn-1-ol 

Downstream Products

• 1224951-98-7 (E)-4-(4-trifluoromethylphenyl)but-3-enyl methanesulfonate 
• 1426692-62-7 3-chloro-2-(4-(trifluoromethyl)phenyl)tetrahydrofuran 

Relevant academic research and scientific papers

Intramolecular N-Me and N-H aminoetherification for the synthesis ofN-unprotected 3-amino-O-heterocycles

A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a va

An Enzymatic Platform for the Highly Enantioselective and Stereodivergent Construction of Cyclopropyl-δ-lactones

Abiological enzymes offers new opportunities for sustainable chemistry. Herein, we report the development of biological catalysts derived from sperm whale myoglobin that exploit a carbene transfer mechanism for the asymmetric synthesis of cyclopropane-fused-δ-lactones, which are key structural motifs found in many biologically active natural products. While hemin, wild-type myoglobin, and other hemoproteins are unable to catalyze this reaction, the myoglobin scaffold could be remodeled by protein engineering to permit the intramolecular cyclopropanation of a broad spectrum of homoallylic diazoacetate substrates in high yields and with up to 99 % enantiomeric excess. Via an alternate evolutionary trajectory, a stereodivergent biocatalyst was also obtained for affording mirror-image forms of the desired bicyclic products. In combination with whole-cell transformations, the myoglobin-based biocatalyst was used for the asymmetric construction of a cyclopropyl-δ-lactone scaffold at a gram scale, which could be further elaborated to furnish a variety of enantiopure trisubstituted cyclopropanes.

Nickel Catalyzed Regio-, Diastereo-, and Enantioselective Cross-Coupling of 3,4-Epoxyalcohol with Aryl Iodides

The first catalytic, regioselective cross-coupling of 3,4-epoxyalcohol with aryl iodides is reported. The combination of NiCl2·DME and a newly developed C2-symmetric oxazoline ligand plays a key role in selective ring opening of seve

Alkene Dioxygenation with Malonoyl Peroxides: Synthesis of γ-Lactones, Isobenzofuranones, and Tetrahydrofurans

Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, γ-lactones, and isobenzofuranones in 44-82% yield and up to 27:1 trans selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.

Copper-Catalyzed Diastereoselective Synthesis of Trifluoromethylated Tetrahydrofurans

The copper-catalyzed intramolecular diastereoselective trifluoromethylcycloetherification of homoallylic alcohols with Togni's reagent as trifluoromethylating reagent was realized under mild conditions. Various trifluoromethylated tetrahydrofurans were synthesized in moderate to good yields. Moreover, a wide range of common functional groups was tolerated.

Asymmetric 5-endo chloroetherification of homoallylic alcohols toward the synthesis of chiral β-chlorotetrahydrofurans

An asymmetric 5-endo chloroetherification of homoallylic alcohols is successfully developed that employs an easily available quaternary ammonium salt derived from cinchonine as a conventional organocatalyst. This approach provides ready access to β-chloro

Stereospecific synthesis of cyclobutylboronates through copper(I)-catalyzed reaction of homoallylic sulfonates and a diboron derivative

A copper(I)-catalyzed stereospecific reaction for the preparation of cis- and trans-1-silyl-2-borylcyclobutanes as well as 1-phenyl-2-borylcyclobutanes is reported. (Z)- and (E)-Homoallylic methanesulfonates were converted to the corresponding trans- and