831192-69-9

Upstream product

• 186249-76-3 (R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide 
• 627-15-6 1,3-dibromopropene 
• 1730-25-2 allylmagnesium bromide 
• 196929-85-8 (R)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 100-52-7 benzaldehyde 
• 107-18-6 allyl alcohol 
• 1208066-51-6 (R_S,S)-N-(1-(phenyl)but-3-yn-1-yl)-2-methylpropane-2-sulfinamide 
• 106-95-6 allyl bromide 
• 688-61-9 Triallylborane 

Downstream Products

• 1190958-62-3 (2R,2'S)-N-tert-butylsulfonyl-2-(2-amino-2-phenylethyl)oxirane 
• 1190958-64-5 (2S,2'S)-N-tert-butylsulfonyl-2-(2-amino-2-phenylethyl)oxirane 
• 130887-64-8 (S)-1-phenylbut-3-en-1-amine hydrochloride 

Relevant academic research and scientific papers

Homoallylic amines as efficient chiral inducing frameworks in the conjugate addition of amides to α,β-unsaturated esters. An entry to enantio-enriched diversely substituted amines

The diastereoselective conjugate addition of secondary homoallylamines, obtained in the enantioenriched form via allylmetallation of imines, to α,β-unsaturated esters is reported. This method allows access to valuable building blocks as well as heterocyclic skeletons, providing tertiary amines bearing two chains integrating a stereogenic center adjacent to the nitrogen atom.

Indium mediated allylation of WteRR-butanesulftnyl imines with 1,3-dibromopropene: Stereoselective synthesis of aziridines

- The reaction of TV-fer?-butanesulfinyl imines 1 with 1,3-dibromopropene (2), in the presence of indium metal, in saturated aqueous solution of sodium bromide, produced bromohomoallylamine derivatives 3 with total facial diastereoselectivity for the imine addition, and moderate yields. These compounds were easily transformed into the corresponding vinyl aziridines 5 upon deprotonation with KHMDS in THF, the intramolecular cyclization taking place in a stereospecific manner in moderate to high yields.

Adducts of Triallylborane with Ammonia and Aliphatic Amines as Stoichiometric Allylating Agents for Aminoallylation Reaction of Carbonyl Compounds

Triallylborane-amines adducts are effective stoichiometric allylating agents in the aminoallylation reaction of carbonyl compounds in methanol. Moreover, copper-catalyzed diastereoselective allylation of Ellman's imine was achieved with triallylborane-methylamine adduct.

New enolate-carbodiimide rearrangement in the concise synthesis of 6-amino-2,3-dihydro-4-pyridinones from homoallylamines

Three-step synthesis of 6-amino-2,3-dihydro-4-pyridinones from homoallylamines involving NBS-mediated cyclization of N-(3-butenyl)ureas to 6-(bromomethyl)-2-iminourethanes, dehydrohalogenation and a novel rearrangement as a key step has been developed. Th

2,2- and 2,6-diarylpiperidines by aryl migration within lithiated urea derivatives of tetrahydropyridines

2-Aryltetrahydropyridines formed by anionic cyclization or ring-closing metathesis were converted to their N′-aryl urea derivatives. Depending on the position of the unsaturation within the tetrahydropyridine ring, metalation by deprotonative lithiation or carbolithiation led to migration of the N′-aryl substituent to the 2- or 6-position via intramolecular nucleophilic attack of a benzylic organolithium on the aryl ring. The products are a range of 2,2-, 2,2,3-, and 2,6-polysubstituted piperidine derivatives. Related chemistry was observed in pyrroline homologues.

Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines: Dual stereocontrol with nearly perfect diastereoselectivity

Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines has been described. Dual stereocontrol, through the combination of a chiral auxiliary and a chiral copper complex, has played an important role in achieving the nearly perfect d

Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols

The palladium-catalyzed allylation of N-tert-butanesulfinyl imines with allylic alcohols in the presence of InI as reducing reagent takes place with high diastereoselectivity in reasonable yields. The reaction with crotyl alcohol is totally regioselective

Synthesis of enantiopure 5-substituted 2,3-methanopyrrolidines by cyclization of enantiopure α-Branched α-N-homoallylamino nitriles

The preparation of 5-substituted 2,3-methanopyrrolidines by the stereoselective cyclization of zincated -amino nitriles derived from enantiopure -branched homoallylamines has been investigated. The formation of trans adducts in excellent diastereoselectiv

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.

Highly diastereoselective zinc-catalyzed propargylation of tert-butanesulfinyl lmines

(Chemical Equetion Presentation) A zinc-catalyzed diastereoselective propargylation of t-butanesulfinyl imines is presented. The methodology provided both aliphatic and aryl homopropargylic amines in up to 98:2 and 99.8:0.2 dr, respectively. The utility of the homopropargylic amines was demonstrated by the application to the synthesis of a cis-substituted pyrido-indole through a diastereoselective Pictet-Spengler cyclization.