Aziridinium Salts

The formation and use of aziridinium salts for stereoselective cyclizations have been studied in pyrrolidine and piperidine ring systems.

A) Cyclizations of N-alkoxyamines

meth4A

Primary references: Tet. Lett. 1989, 30, 1327-1330; Tet. Lett. 1989, 30, 1331-1334.

B) Stereocontrolled double cyclizations in studies of Stemona alkaloids

meth4B

Primary references: For synthesis of croomines: J. Am. Chem. Soc. 1989, 111, 1923-1925.
Synthesis of (-)-stemospironine: Org. Lett. 2001, 3, 2721-2724.
Synthesis of (-)-stemonine: Org. Lett. 2003, 5, 3361-3364.
Synthesis of trans-2,6-disubstituted piperidines: Heterocycles  2004, 64, 45-50.