1131796-18-3

Basic information

• Product Name: trans-2-phenyl-3-(1-naphthyl)-1-(2-trimethylsilylethanesulfonyl)-aziridine
• CAS NO: 1131796-18-3
• Molecular Weight: 409.624
• Mol File: 1131796-18-3.mol

Chemical Properties

• CAS DataBase Reference: trans-2-phenyl-3-(1-naphthyl)-1-(2-trimethylsilylethanesulfonyl)-aziridine(CAS DataBase Reference)
• NIST Chemistry Reference: trans-2-phenyl-3-(1-naphthyl)-1-(2-trimethylsilylethanesulfonyl)-aziridine(1131796-18-3)
• EPA Substance Registry System: trans-2-phenyl-3-(1-naphthyl)-1-(2-trimethylsilylethanesulfonyl)-aziridine(1131796-18-3)

Safety Data

• Hazardous Substances Data: 1131796-18-3(Hazardous Substances Data)

Relevant articles and documents

Highly enantioselective aziridination of N-protected imines: Comparison of the phosphazene EtP2 and sodium hydride as bases

Asymmetric synthesis of 2,3-disubstituted N-Boc, N-SES, and N-Ts aziridines starting from N-protected imines, using sulfonium salt derived from Eliel's oxathiane, is reported. Sodium hydride was successfully used as a substitute for the phosphazene base EtP2 without any loss of yield, enantioselectivity, or diastereoselectivity. Georg Thieme Verlag Stuttgart.

Sulfur ylide promoted synthesis of N-protected aziridines: A combined experimental and computational approach

A range of N-protected aziridines [N-Tosyl (N-Ts), N-2- trimethylsilylethanesulfonamide (N-SES), N-tertbutoxycarbonylamido (N-Boc), and N-o-nitrobenzenesulfonamide (oNs)] were prepared in moderate to good yield and with high enantiomeric excess of both isomers starting from N-protected imines, using a sulfonium salt derived from Eliel's oxathiane. The diastereoselectivities of the reactions are influenced by the imine N-protecting group, the imine substituent, and the sulfide structure. An unusual cis selectivity was observed in the formation of N-tosyl-2-phenyl-3-tert- butylaziridine and N-o-trimethylsilylethanesulfonamide-2-phenyl-3-tert- butylaziridine, which was explained by using computational models. The analysis suggests that betaine formation in the case of N-tosyl-tert-butylaldimine aziridination using oxathiane benzyl sulfonium ylide 1′ is reversible and that the selectivity is determined at the rotation step, which is unusual for semistabilized ylide aziridination. We have shown herein that the steric bulk of an imine substituent, in combination with a sterically demanding sulfonium ylide, can also affect the reversibility of the reaction. This is the first example of this sort involving aziridinations using semistabilized ylides.