1023743-85-2

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 186249-76-3 (R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide 
• 196929-85-8 (R)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 100-52-7 benzaldehyde 

Downstream Products

• 325490-29-7 (1R)-1-phenylprop-2-en-1-amine 
• 688362-39-2 N-[(1R)-1-phenylprop-2-en-1-yl]benzamide 
• 1181394-16-0 (R)-1-phenylprop-2-en-1-amine hydrochloride 

Relevant academic research and scientific papers

Transition metal-free trifluoromethylation of n-Allylamides with sodium Trifluoromethanesulfinate: Synthesis of Trifluoromethyl-containing oxazolines

A transition metal-free method for the trifluoromethylation of N-allylamides has been developed, and the corresponding trifluoromethylcontaining oxazolines were prepared in moderate to good yields. The protocol uses readily available substituted N-allylamides as the starting materials, inexpensive and easily stored sodium trifluoro- ACHTUNGTRENUNGmethanesulfinate as the trifluoromethyl source, iodobenzene diacetate as the oxidant, and the procedure involves sequential intermolecular trifluoromethylation of alkenes with sodium trifluoro- ACHTUNGTRENUNGmethanesulfinate and intramolecular cyclization. This is the first example to prepare CF3-containing oxazolines. Therefore, the present method should afford an efficient and practical strategy for synthesis of other CF3-containing cyclic compounds.

Simple N-sulfinyl-based chiral sulfur-olefin ligands for rhodium-catalyzed asymmetric 1,4-additions

A variety of N-sulfinyl-based chiral sulfur-olefin ligands has been successfully developed for the first time for rhodium-catalyzed highly efficient and enantioselective 1,4-additions. The ease of synthesis and needless consideration of the carbon chirality makes this novel type of ligands attractive for asymmetric catalysis.

Asymmetric synthesis of α- And β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl) imines

The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected α- and β-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, α-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. α,α- Disubstituted α-amino esters with high enantiomeric purity can also be prepared when α-imino esters are the starting substrates.

An improved procedure for the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines: use of catalytic dialkylzinc

The addition of triorganozincates to (R)-N-(tert-butanesulfinyl)benzaldimine has been performed with very good results by using a catalytic amount of Me2Zn (0.15 equiv) to generate the organozincate. Yields and/or diastereoselectivities of the

Application of the addition of triorganozincates to N-(tert-butanesulfinyl)imines to the enantioselective synthesis of α-amino acids

Highly enantiomerically enriched N-protected α-amino acids can be easily prepared from optically pure N-(tert-butanesulfinyl)imines by a four-step sequence involving: diastereoselective addition of a triorganozincate to the imine, removal of the sulfinyl group, benzoylation of the nitrogen atom of the obtained primary amine and oxidation of one of the substituents on the carbon atom α to the nitrogen. Using the same configuration in the sulfinyl chiral auxiliary, amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. α,α-Disubstituted α-amino esters with high optical purity can also be prepared by the diastereoselective addition of trialkylzincates to α-imino esters.

Synthesis of highly enantiomerically enriched amines by the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines

The reaction of triorganozincates with (R)-N-(tert-butanesulfinyl) imines gives the expected α-branched sulfinamides in good to excellent yields with diastereomeric ratios of up to 98:2. The N-sulfinyl group of the products can be easily removed by acidic treatment, affording the corresponding chiral primary amines in enantiomeric excesses of up to 96%. The reactivity and the selectivity shown by the triorganozincates are different from the ones observed with the corresponding Grignard reagents, which allows, in several cases, the preparation of both enantiomers of an amine from the same imine substrate. When mixed triorganozincates are used, one can take advantage of the slow transfer rate of the methyl group to use it as a non-transferable one. Both aromatic and aliphatic aldimines, as well as activated ketimines, are good substrates for these addition reactions.

Asymmetric synthesis of chiral amines by highly diastereoselective 1,2- additions of organometallic reagents to N-tert-butanesulfinyl imines

High yielding and highly diastereoselective methods for 1,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) and N-tert- butanesulfinyl kerimines (3) are described. The additions of alkyl, aryl, alkenyl, and allyl carbanions to a diverse set of imines with different steric and electronic properties are demonstrated. Acidic methanolysis of the sulfinamide products (4 and 6) delivers highly enantioenriched α-branched and α,α-dibranched amines. Since a broad range of sulfinyl imines are easily accessible from aldehydes and ketones, a wide variety of enantioentriched amines may be prepared.