885315-17-3

Upstream product

• 885315-11-7 2-Methyl-propane-2-sulfinic acid ((R)-1-ethoxy-2,2,2-trifluoro-ethyl)-amide 
• 1219607-83-6 (S_S)-2-methyl-N-(2,2,2-trifluoroethylidene)-propane-2-sulfinamide 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 75-46-7 trifluoromethan 
• 862776-58-7 (S)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 100-52-7 benzaldehyde 
• 929642-48-8 (S,E)-2-methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide 

Downstream Products

• 128404-37-5 (S)-2,2,2-trifluoro-1-phenylethan-1-amine hydrochloride 

Relevant academic research and scientific papers

Asymmetric addition reactions of Grignard reagents to chiral 2-trifluoromethyl tert-butyl (Ellman) sulfinimine-ethanol adducts

The addition of Grignard reagents to chiral trifluoromethyl tert-butyl sulfinimine-ethanol adducts affords protected trifluoromethylamines in high yields with good to excellent diastereoselectivities. The stereochemical outcome of the addition is opposite to that expected via a chelation controlled transition state.

Gas/Liquid-Phase Micro-Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N-Sulfinylimines

A micro-flow nucleophilic trifluoromethylation of carbonyl compounds using gaseous fluoroform was developed. This method also allows the first micro-flow transformation of N-sulfinylimines into trifluoromethyl amines with excellent diastereoselectivity. To demonstrate the synthetic utility of this micro-flow synthesis, the formal micro-flow synthesis of Efavirenz is described.

METHOD FOR PRODUCING OPTICALLY ACTIVE TRIFLUOROMETHYL GROUP-CONTAINING AMINO ACID DERIVATIVE

PROBLEM TO BE SOLVED: To provide methods for producing optically active trifluoromethyl group-containing sulfinamide derivatives and optically active amino acids/hydrochlorides, using trifluoromethane as a generator of trifluoromethyl anions. SOLUTION: Th

Stereodivergent trifluoromethylation of: N -sulfinylimines by fluoroform with either organic-superbase or organometallic-base

Here we have successfully demonstrated the first stereodivergent direct nucleophilic trifluoromethylation of N-sulfinylimines using the potent greenhouse gas "HFC-23, fluoroform" with an organic-superbase or an organometallic-base in high yields and selectivity.

Diastereoselective addition of organomagnesium and organolithium reagents to chiral trifluoromethyl N-tert-butanesulfinyl hemiaminals

The asymmetric synthesis of trifluoromethylated tertiary and secondary carbinamines (α,α-dibranched and α-branched amines) was achieved by reaction of alkyl, aryl and allyl organomagnesium or organolithium reagents to trifluoromethyl N-tert-butanesulfinyl

Trifluoroacetaldehyde: A useful industrial bulk material for the synthesis of trifluoromethylated amino compounds

The synthesis of various trifluoromethylated amino compounds was studied using trifluoroacetaldehyde, an industrial bulk material, as a starting compound. One general application of trifluoroacetaldehyde is the preparation of trifluoroethylamino derivatives via reductive amination reaction. This synthesis includes the formation of the corresponding N,O-acetal intermediates followed by their reduction using NaBH4 or 2-picoline borane complex, affording the target trifluoroethylamino compounds in moderate to good yields (47-87%). Another general application of trifluoroacetaldehyde is the synthesis of chiral α-substituted trifluoroethylamino compounds. In this synthesis, trifluoroacetaldehyde was first converted into the chiral trifluoromethyl tert-butyl sulfinimine, which was subjected to 1,2-nucleophilic addition reactions across its C{double bond, long}N double bond. The addition of phenyllithium afforded α-(phenyl)trifluoroethylamino derivative in 83% yield and with 96% de. Allylation and Reformatsky reactions produced the corresponding α-substituted trifluoroethylamino derivatives in 82 and 58% yields and with 90 and 91% de, respectively.

Rhodium-catalyzed diastereoselective 1,2-addition of arylboronic acids to chiral trifluoroethyl imine

Rhodium-catalyzed 1,2-addition of arylboronic acids 4a-j to chiral trifluoroethyl imine 3 afforded diastereomerically enriched sulfinamides 5a-j. The chiral auxiliary of the sulfinamide products was readily removed under acidic methanolysis to provide the corresponding trifluoroethylamine analogs 6a-j.

Asymmetric syntheses of 1-Aryl-2,2,2-trifluoroethylamines via diastereoselective 1,2-addition of arylmetals to 2-Methyl-N-(2,2,2- trifluoroethylidene)propane-2-sulfinamide

Condensation of N-tert-butanesulfinamide (S)-1 with trifluoroacetaldehyde hydrate 2a afforded 2-methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide 3. Without isolation and purification, imine 3 was added to various aryllithium reagents to give high