INVESTIGADORES
DI CHENNA Pablo Hector
artículos
Título:
Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses
Autor/es:
DI CHENNA PABLO H.; DAUBAN, P.; GHINI, ALBERTO A.; BURTON, GERARDO; DODD, R. H.
Revista:
TETRAHEDRON LETTERS
Editorial:
Elsevier
Referencias:
Año: 2000 vol. 41 p. 7041 - 7045
ISSN:
0040-4039
Resumen:
The copper-catalyzed reaction of [N-(Ses)imino]phenyliodinane with 11-pregnene-3,20-dione gave the corresponding aziridine in 53% yield. The Ses protecting group could be conveniently removed using the TASF reagent. Furthermore, nucleophilic ring opening of the protected N-Ses-aziridine with thiophenol in the presence of a Lewis acid led to introduction of the thiophenol group at the a-12 position but, unexpectedly, concomitant loss of the Ses group to provide compound 10.N-(Ses)imino]phenyliodinane with 11-pregnene-3,20-dione gave the corresponding aziridine in 53% yield. The Ses protecting group could be conveniently removed using the TASF reagent. Furthermore, nucleophilic ring opening of the protected N-Ses-aziridine with thiophenol in the presence of a Lewis acid led to introduction of the thiophenol group at the a-12 position but, unexpectedly, concomitant loss of the Ses group to provide compound 10.
