143371-09-9

Upstream product

• 143371-08-8 (S)-methyl 3-(4-methylphenylsulfonamido)-3-phenylpropanoate 
• 1000979-81-6 4-methyl-N-(3-oxo-1-phenyl-propyl)-benzenesulfonamide 
• 357417-35-7 (3S)-3-{[(4-methylphenyl)sulfonyl]amino}-3-phenylpropanoic acid 
• 875-74-1 (R)-phenylglycine 
• 56613-80-0 D-2-phenylglycinol 
• 1001060-81-6 (3S)-(4-toluenesulfonyl)amino-3-phenylpropionitrile 
• 118917-59-2 (R)-N-(2-hydroxy-1-phenylethyl)-4-methyl-S-methylenebenzenesulfinamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 1275616-34-6 methyl (R,R)-2-chloro-3-phenyl-3-(p-toluenesulfonylamino)propanimidate hydrochloride 
• 1275616-39-1 methyl (R,R)-2-chloro-3-phenyl-3-(p-toluenesulfonylamino)propanoate 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 

Downstream Products

• 936011-91-5 (S)-2-phenyl-1-tosylazetidine 
• 143371-10-2 N-((S)-3-Bromo-1-phenyl-propyl)-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

Palladium-Catalyzed Regioselective and Stereospecific Ring-Opening Suzuki-Miyaura Arylative Cross-Coupling of 2-Arylazetidines with Arylboronic Acids

We have developed a palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki–Miyaura arylative cross-coupling of N-tosyl-2-arylazetidines to give enantioenriched 3,3-diarylpropylamines. This reaction represents an example of transition-metal-catalyzed ring-opening cross-coupling using azetidines as a non-classical alkyl electrophile. Density functional theory rationalized the mechanism of the full catalytic cycle, which consists of the selectivity-determining ring opening of the azetidine, reaction with water, rate-determining transmetalation, and reductive elimination. Transition states of the selectivity-determining ring-opening step were systematically determined by the multi-component artificial force induced reaction (MC-AFIR) method to explain the regioselectivity of the reaction. (Figure presented.).

Phosphine Oxide-Sc(OTf)3 Catalyzed Highly Regio- and Enantioselective Bromoaminocyclization of (E)-Cinnamyl Tosylcarbamates. An Approach to a Class of Synthetically Versatile Functionalized Molecules

A highly regio- and enantioselective bromoaminocyclization of (E)-cinnamyl tosylcarbamates catalyzed by a chiral phosphine oxide-Sc(OTf)3 complex is described. A wide variety of optically active aryl 5-bromo-1,3-oxazinan-2-ones can be obtained

Asymmetric synthesis of α-chloro-β-amino-N-sulfinyl imidates as chiral building blocks

New chiral α-chloro-β-amino-N-sulfinyl imidates were synthesized in high yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of (RS)-methyl N-tert-butanesulfinyl-2- chloroethanimidate with aromatic aldimin

N-heterocyclic carbene-catalyzed enantioselective mannich reactions with α-aryloxyacetaldehydes

(Chemical Equation Presented) N-Heterocyclic carbenes (NHCs) catalyze a new Mannich-type reaction to form β-amino acid derivatives in high yield and enantioselectivity. The reaction is initiated by the addition of an NHC to an C-aryloxyaldehyde followed by elimination of a phenoxide anion which generates an enol/enolate. A Mannich addition to a tosylimine proceeds with excellent control over enantioselectivity. In a new carbene catalysis concept, catalyst regeneration is promoted by return, or rebound, and acylation of the phenoxide group which served as the activating component in the first step of the catalytic cycle. The activated ester products formed in situ are manipulated to form a variety of useful compounds including β-amino acids, β-amino amides, and peptides.

A convenient synthetic route to enantiopure N-tosylazetidines from α-amino acids

A general and convenient synthetic route to various chiral 2-substituted- and 2,4-disubstituted-N-tosylazetidines (ee >99%) is described in good overall yields starting from chiral α-amino acids using very simple chemistry.