17330-25-5

Upstream product

• 18085-37-5 methyl 1-benzyl-2-azetidinecarboxylate 
• 98-59-9 p-toluenesulfonyl chloride 
• 255882-72-5 azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 29547-04-4 methyl 2,4-dibromobutanoate 
• 10019-95-1 N-tosylpyrrolidinone 
• 67-56-1 methanol 
• 178946-64-0 3-bromo-1-tosylpyrrolidin-2-one 

Downstream Products

• 17330-26-6 (1-tosylazetidin-2-yl)methanol 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 3899-91-0 4-methoxyphenyl p-toluenesulfonate 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 97478-25-6 2-((3E)-4-phenyl-1,3-butadienyl)-1-tosylazetidine 
• 124994-26-9 2-(E-2-phenylethenyl)-1-tosyl-3,4-dehydropiperidine 
• 911818-36-5 4-methyl-N-(2-(2-oxocyclobutyl)ethyl)benzenesulfonamide 

Relevant academic research and scientific papers

Cleavage of activated cyclic amines: Unprecedented approach toward 2-substituted cyclobutanones

(Chemical Equation Presented) We report, for the first time, ring opening of activated four- to six-membered cyclic amines followed by an intramolecular expansion of cyclopropanol to cyclobutanone via carbocation intermediate. In the case of a N-tosylazir

Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams

2-Carboxylated aza-rings have been synthesized in two steps through a highly selective monohalogenation of N-sulfonylated lactams of various ring sizes (from 5- to 8-membered rings) followed by a ring contraction reaction. The selective monohalogenation of N-sulfonyl lactams has been achieved in modest to excellent yields (9 examples, 39–96%) using N-halogenosuccinimides via the in situ generation of trimethylsilyl ketene aminal derivatives. The so-obtained α-halogeno N-sulfonyl lactams were engaged in a ring opening/ring closing reaction in the presence of various alcohols or anilines under basic conditions affording 2-carboxylated aza-rings, such as azetidine, pyrrolidine or piperidine derivatives in high yields (24 examples, 61–99%).

Robust synthesis of N-sulfonylazetidine building blocks via ring contraction of α-bromo N-sulfonylpyrrolidinones

A simple and robust one-pot nucleophilic addition-ring contraction of α-bromo N-sulfonylpyrrolidinones has been achieved toward α-carbonylated N-sulfonylazetidines. In the presence of potassium carbonate, various nucleophiles, such as alcohols, phenols or anilines, have been efficiently incorporated into the azetidine derivatives. Moreover, the α-bromopyrrolidinone precursors could be selectively obtained in good yields by monobromination of cheap and easily available N-sulfonyl-2-pyrrolidinone derivatives.

Preparation comprising an enzyme for asymmetrical hydrolysis of N-substituted C3-C4 cyclic imino-2-carboxylic acid ester and method of using the same

There is disclosed an enzyme preparation comprising: (i) a styrene-divinylbenzene copolymer having fine pores with an average radius of 200 - 500?, and (ii) an enzyme capable of asymmetrically hydrolyzing N-substituted C3-C4 cyclic imino-2-carboxylic acid ester to preferentially produce an (S)-N-substituted C3-C4 cyclic imino-2-carboxylic acid, wherein said enzyme comprises an amino acid sequence as set forth in SEQ ID NO: 1 or the like.

TRANSFORMATION OF N-TOSYL-2-(1,3-BUTADIENYL)AZIRIDINE INTO N-TOSYL-2-ETHENYL-3-PYRROLINE.

1,3-Butadienylaziridines or 1,3-butadienylazetidines activated by N-tosyl group smoothly rearrange to vinylpyrroline derivatives or vinylpiperidines in the presence of a catalytic amount of Pd(PPh3)4.Triphenyltin radical induced rearrangement of title compounds is also described.