Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses

Authors
Di Chenna, PH Dauban, P Ghini, A Burton, G Dodd, RH
Citation
Ph. Di Chenna et al., Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses, TETRAHEDR L, 41(36), 2000, pp. 7041-7045
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
36
Year of publication
2000
Pages
7041 - 7045
Database
ISI
SICI code
0040-4039(20000902)41:36<7041:AO1UP>2.0.ZU;2-O
Abstract
The copper-catalyzed reaction of [N-(Ses)imino]phenyliodinane with 11-pregn ene-3,20-dione gave the corresponding aziridine in 53% yield. The Ses prote cting group could be conveniently removed using the TASF reagent. Furthermo re, nucleophilic ring opening of the protected N-Ses-aziridine with thiophe nol in the presence of a Lewis acid led to introduction of the thiophenol g roup at the alpha-12 position but, unexpectedly, concomitant loss of the Se s group to provide compound 10. (C) 2000 Elsevier Science Ltd. All rights r eserved.