936011-91-5

Basic information

• Product Name: (S)-2-phenyl-1-tosylazetidine
• Synonyms: (S)-2-phenyl-1-tosylazetidine
• CAS NO: 936011-91-5
• Molecular Weight: 287.382
• Mol File: 936011-91-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-2-phenyl-1-tosylazetidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-phenyl-1-tosylazetidine(936011-91-5)
• EPA Substance Registry System: (S)-2-phenyl-1-tosylazetidine(936011-91-5)

Safety Data

• Hazardous Substances Data: 936011-91-5(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 37088-67-8 methyl (3R)-3-amino-3-phenylpropanoate 
• 936012-06-5 C₁₆H₁₇NO₄S 
• 883458-37-5 (R)-(+)-methyl 3-(4-methylphenylsulfonamido)-3-phenylpropanoate 
• 158009-86-0 (S_S,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate 
• 153277-49-7 (S)-N-benzylidene-4-toluenesulfinamide 
• 357417-35-7 (3S)-3-{[(4-methylphenyl)sulfonyl]amino}-3-phenylpropanoic acid 
• 118917-59-2 (R)-N-(2-hydroxy-1-phenylethyl)-4-methyl-S-methylenebenzenesulfinamide 
• 1001060-81-6 (3S)-(4-toluenesulfonyl)amino-3-phenylpropionitrile 
• 56613-80-0 D-2-phenylglycinol 
• 875-74-1 (R)-phenylglycine 
• 1000979-81-6 4-methyl-N-(3-oxo-1-phenyl-propyl)-benzenesulfonamide 
• 143371-09-9 (S)-N-(3-hydroxy-1-phenylpropyl)-4-methylbenzenesulfonamide 

Downstream Products

• 928007-62-9 (R)-N-(3-hydroxy-3-phenylpropyl)-4-methyl-benzenesulfonamide 
• 32121-04-3 N-cinnamyl-4-methylbenzenesulfonamide 

Relevant articles and documents

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.).

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.