186801-24-1

Upstream product

• 186800-93-1 N-[(Z)-(1S,4S)-1-Isobutyl-4-(2-methoxy-ethoxymethoxy)-pent-2-enyl]-2,4,6-trimethyl-benzenesulfonamide 
• 214751-99-2 (E,2S,5S)-7-methyl-2-phenyl-5-N-[(2,4,6-trimethylbenzene)sulfonyl]aminooct-3-ene 
• 186800-71-5 2,4,6-Me₃C₆H₂-SO₂NSO 
• 148838-30-6 N-(3-methylbutylidene)-2,4,6-trimethylbenzenesulfonamide 
• 148838-36-2 (1S,2E,4S)-N-<2-bromo-4-<(2-methoxyethoxy)methoxy>-1-(2-methylpropyl)-2-pentenyl>-2,4,6-trimethylbenzenesulfonamide 
• 4543-58-2 2,4,6-trimethylbenzenesulfonamide 
• 214752-00-8 (E,2R,5S)-7-methyl-5-(2,4,6-trimethylbenzenesulfonyl)amino-2-phenyloct-3-ene 

Downstream Products

• 186801-25-2 (3S,4S)-3-Hydroxy-2,2,6-trimethyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-heptanoic acid methyl ester 

Relevant academic research and scientific papers

Reactions of n-arylsulfonyl-2,3-cis- and n-arylsulfonyl-2,3-frans-3-alkyl-2-vinylaziridines with organocopper reagents: importance of 2,3-cis-stereochemistry in controlling regio- and stereoselectivity

Although reactions of 2,3-trans-N-arylsulfonyl-3-alkyl-2-alkenylaziridines with organocopper reagents give a mixture of two or three products, the corresponding 2,3-cis-isomers provide a highly efficient route to synthetically important nonracemic CE)-allylamines. It is also found that the reaction proceeds via the well-known anti-SN2′ pathway.

α-Amino acids and N-protected α-amino aldehydes by stereoselective additions of a chiral vinyllithium reagent to sulfonylimines

The chiral vinyllithium reagent (S)-1b, readily generated from dibromoalkene (S)-1a by bromine/lithium exchange, adds stereoselectively to mesitylsulfonylimines 2a-f so that the diastereomers 3 are obtained in ≥98% d.e. after column chromatography. The bromoalkenes 3a-d are submitted to ozonolysis in methanol to give α-mesitylsulfonylamino esters (S)-8a-d which can be hydrolyzed to deliver N-protected α- amino acids in >95% e.e. On the other hand, α-mesitylsulfonylamino aldehydes 12a-d are available when bromoalkenes 3a, d-f are first debrominated (→ 11a-d) and subsequently ozonized. In order to avoid reacemization, the aldehydes 12a-d are not purified but submitted to a Mukaiyama-type aldol addition whereby hydroxyesters 15a-d are formed as single diastereomers in a chelate-controlled reaction. The relative configuration of the esters 15a-d is proven by conversion into the oxazolidinones 16a-d whose optical purity is determined to exceed 92% e.e. by 1H-NMR measurements in the presence of chiral shift reagents. The sulfonylimine 21a and a series of para-substituted derivatives 21b-h are also allowed to react with the vinyllithium reagent 1b to give mixtures of diastereomers 22/23. The logarithms of the diastereomeric ratios 22:23 correlate with Hammett's σ-values. VCH Verlagsgesellschaft mbH, 1997.