1376574-08-1

Basic information

• Product Name: methyl N-tosyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate
• CAS NO: 1376574-08-1
• Molecular Weight: 355.412
• Mol File: 1376574-08-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl N-tosyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-tosyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate(1376574-08-1)
• EPA Substance Registry System: methyl N-tosyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate(1376574-08-1)

Safety Data

• Hazardous Substances Data: 1376574-08-1(Hazardous Substances Data)

Upstream product

• 29547-04-4 methyl 2,4-dibromobutanoate 
• 18085-37-5 methyl 1-benzyl-2-azetidinecarboxylate 

Relevant articles and documents

Synthesis of spirocyclopropyl γ-lactams by tandem intramolecular azetidine ring-opening/closing cascade reaction: Synthetic and mechanistic aspects

The scope and limitations of a novel intramolecular azetidine ring-opening/closing cascade reaction affording spirocyclopropyl γ-lactams from azetidines in high regio- and stereoselectivity is reported. The key step of the process is a SN2-type ring-opening of TMSOTf-activated azetidine rings by silyl ketene acetals generated by treatment with TMSOTf and TEA. This study is a very rare example of nucleophilic ring-opening of azetidines that does not require formation of quaternary azetidinium salts by N-alkylation or the use of N-electron-withdrawing groups. Application of this process to 2-azetidinone system led to a complete change in reactivity and provide 6-aza-bicyclo[3.2.0]heptane derivatives via an unprecedented Mukaiyama aldol-like reaction involving an ester acceptor and a silyl imidate.