186801-10-5

Upstream product

• 773-64-8 2-mesitylenesulphonyl chloride 
• 875-74-1 (R)-phenylglycine 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 
• 186801-07-0 methyl (R)-α-<<(2,4,6-trimethylphenyl)sulfonyl>amino>benzeneacetate 

Downstream Products

• 875-74-1 (R)-phenylglycine 
• 1016633-07-0 (R)-N-(2-hydroxy-1-phenylethyl)-2,4,6-trimethylbenzenesulfonamide 
• 866458-32-4 (R)-Phenyl-(2,4,6-trimethyl-benzenesulfonylamino)-acetyl chloride 

Relevant academic research and scientific papers

Efficient synthesis of new chiral 1,2-benzothiazin-3-one 1,1-dioxide derivatives via lateral lithiation of 3-N-mesitylenesulfonyl-1,3-oxazolidin-2-ones

Chiral 3-N-mesitylenesulfonyl-1,3-oxazolidin-2-ones 4a-e derived from (l)- and (d)-amino acids 1a-e undergo lateral lithiation with lithium diisopropylamide and TMEDA in anhydrous THF to provide new optically-active 1,2-benzothiazin-3-one 1,1-dioxide deri

Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalysed epoxidation

New sulfonamide-derived hydroxamic acids 7-11 have been developed as chiral ligands for the V-catalysed asymmetric epoxidation, showing high reactivity at subzero temperatures and moderate to good enantioselectivity. The strong accelerating effect exhibited by the ligands of this type can be attributed to the sulfonamide functionality. A range of cinnamyl type allylic alcohols were epoxidised with up to 74% ee. The Royal Society of Chemistry 2005.

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.