133344-26-0

Upstream product

• 5349-15-5 ethyl 2-((phenylsulfonyl)amino)acetate 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 265669-27-0 N-Phenylsulfonyl-α-methylglycine ethyl ester 
• 173258-39-4 ethyl 4-oxo-1-phenylsulfonylpiperidine-2-carboxylate 
• 133344-09-9 (1S,3S,4R)-2-Benzenesulfonyl-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Asymmetric α-substitution versus aza Diels-Alder reaction of electron deficient N-sulfonyl imines

Several N-arylsulfonylglycine esters have been brominated under photolytic conditions to provide the corresponding α-bromoglycine. These bromo esters can be treated with a range of bases to generate N-sulfonyl imino esters in situ; attempts to isolate the imines in a pure state were universally unsuccessful. Once generated, the imines can be trapped with cyclopcntadiene to provide the corresponding aza Diels-Alder adducts in varying yields, depending upon the base used. In addition, if organometallic bases were employed (alkyllithiums and alkylaluminium reagents), not only were aza Diels-Alder adducts formed, but addition to the imine was also observed. In the case of organoaluminium reagents, imine addition was the major product. This process could be transformed into a stoichiometric asymmetric version, by generating a chiral aluminium reagent in situ to form a trialkyl (or trialkoxy) aluminium reagent, which when reacted with an N-sulfonyl bromoglycinate resulted in 19 to 62% enantiomeric excess of the corresponding substituted glycinate product. The Royal Society of Chemistry 2000.

Diastereoselectivity and assignment of absolute stereochemistry in the aza-Diels-Alder reaction of a sulfonylimino acetate with 1-methoxy-3-trimethylsilyloxybuta-1,3-diene

N-imine 1b generated in situ from the corresponding brominated glycinate 4b reacts with Davishefsky's diene under thermal conditions to give a high yield of diastereoisomeric Diels-Alder adducts 7b and 6b in a 2.04:1 ratio.

IMINO DIELS-ALDER CYCLOADDITIONS: AN APPLICATION TO THE SYNTHESIS OF (+/-)-ARISTEROMYCIN

A formal synthesis of (+/-)-aristeromycin starting from the imino Diels-Alder cycloadduct 3a has been achieved with high overall yield.A novel method for the in situ preparation of N-sulfonylimines is reported.