32933-15-6

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 56157-01-8 N,4-dimethyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide 
• 154010-96-5 1-(p-Toluenesulfonyl)azetidin-3-ol 
• 76543-27-6 1-(p-toluenesulfonyl) azetidin-3-one 
• 100-58-3 phenylmagnesium bromide 
• 17945-94-7 3-phenyl-1-azabicyclo[1.1.0]butane 

Relevant academic research and scientific papers

1,5-rhodium shift in rearrangement of N -arenesulfonylazetidin-3-ols into benzosultams

Benzosultams are synthesized in an enantiopure form starting from α-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by β-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.

Solar-driven incorporation of carbon dioxide into α-amino ketones

Power of the sun: Carbon dioxide was incorporated into α-amino ketones through a consecutive process consisting of a solar-energy-harvesting photocyclization reaction and a nucleophilic CO2 incorporation reaction. The single-flask operation produced amino-substituted cyclic carbonates, thereby presenting a simple model of the chemical utilization of solar energy for CO2 incorporation. R=sulfonyl group. Copyright

Reactions of 3-ethyl- and 3-phenyl-1-azabicyclo[1.1.0]butanes with tosyl chloride and tosyl azide

Reactions of 3-ethyl-1-azabicyclo[1.1.0]butane (4) with TsCl and with TsN3 have been studied in aqueous THF solution and in the presence of a variety of nucleophilic trapping agents. Thus, reaction of 4 with TsCl- Na2CO3 afforded N-p-toluenesulfonyl-3-chloro-3-ethylazetidine (6, 34%), N- (N'-p-toluenesulfonyl-3'-ethyl-3'-azetidinyl)-3-chloro-3-ethylazetidine (7, 3.4%), and N-p-toluenesulfonyl-3-ethyl-3-hydroxyazetidine (8, 31%). When this reaction was repeated in the presence of a tenfold molar excess of NaCl, the yield of 6 increased to 80%, primarily at the expense of 8, which was isolated in only 4.3% yield. When this reaction was performed in the presence of a tenfold molar excess of NAN3, the predominant reaction products were TsN3 (32%) and an inseparable mixture of 6 and N-p-toluenesulfonyl-3-azido- 3-ethylazetidine (9; product ratio 6:9 = 1:1). Finally, 4 reacted with TsN3 under four different sets of reaction conditions. In every case, 9 was the major product isolated from these reactions (32-74%). Similar results were obtained for the corresponding reactions of 3-phenyl-1- azabicyclo[1.1.0]butane (1) with TsCl. All of the results reported herein are consistent with expectations based upon a mechanism that involves nucleophilic trapping of a putative tertiary carbocationic intermediate.

N-Acyl-3-azetidinone

Disclosed herein are novel N-acyl-3-aryl-3-azetidinols useful as intermediates. A method is provided for their direct preparation from acyclic starting materials. These N-acyl-3-aryl-azetidinols provide a convenient route to the 3-azetidinol series.