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

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 thiophe...

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Detalles Bibliográficos
Autores principales:	Di Chenna, Pablo Héctor, Ghini, Alberto Antonio, Burton, Gerardo
Publicado:	2000
Materias:	11 pregnene 3,20 dione aziridine derivative pregnane derivative steroid unclassified drug article chemical reaction nuclear Overhauser effect proton nuclear magnetic resonance reduction stereochemistry stereoisomerism steroidogenesis synthesis
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v41_n36_p7041_DiChenna http://hdl.handle.net/20.500.12110/paper_00404039_v41_n36_p7041_DiChenna
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00404039_v41_n36_p7041_DiChenna
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spelling	paper:paper_00404039_v41_n36_p7041_DiChenna2023-06-08T15:04:26Z Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses Di Chenna, Pablo Héctor Ghini, Alberto Antonio Burton, Gerardo 11 pregnene 3,20 dione aziridine derivative pregnane derivative steroid unclassified drug article chemical reaction nuclear Overhauser effect proton nuclear magnetic resonance reduction stereochemistry stereoisomerism steroidogenesis synthesis 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 α-12 position but, unexpectedly, concomitant loss of the Ses group to provide compound 10.© 2000 Elsevier Science Ltd. Fil:Di Chenna, P.H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ghini, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2000 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v41_n36_p7041_DiChenna http://hdl.handle.net/20.500.12110/paper_00404039_v41_n36_p7041_DiChenna
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	11 pregnene 3,20 dione aziridine derivative pregnane derivative steroid unclassified drug article chemical reaction nuclear Overhauser effect proton nuclear magnetic resonance reduction stereochemistry stereoisomerism steroidogenesis synthesis
spellingShingle	11 pregnene 3,20 dione aziridine derivative pregnane derivative steroid unclassified drug article chemical reaction nuclear Overhauser effect proton nuclear magnetic resonance reduction stereochemistry stereoisomerism steroidogenesis synthesis Di Chenna, Pablo Héctor Ghini, Alberto Antonio Burton, Gerardo Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses
topic_facet	11 pregnene 3,20 dione aziridine derivative pregnane derivative steroid unclassified drug article chemical reaction nuclear Overhauser effect proton nuclear magnetic resonance reduction stereochemistry stereoisomerism steroidogenesis synthesis
description	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 α-12 position but, unexpectedly, concomitant loss of the Ses group to provide compound 10.© 2000 Elsevier Science Ltd.
author	Di Chenna, Pablo Héctor Ghini, Alberto Antonio Burton, Gerardo
author_facet	Di Chenna, Pablo Héctor Ghini, Alberto Antonio Burton, Gerardo
author_sort	Di Chenna, Pablo Héctor
title	Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses
title_short	Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses
title_full	Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses
title_fullStr	Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses
title_full_unstemmed	Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses
title_sort	aziridination of 11-pregnene-3,20-dione using phi=n-ses
publishDate	2000
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v41_n36_p7041_DiChenna http://hdl.handle.net/20.500.12110/paper_00404039_v41_n36_p7041_DiChenna
work_keys_str_mv	AT dichennapablohector aziridinationof11pregnene320dioneusingphinses AT ghinialbertoantonio aziridinationof11pregnene320dioneusingphinses AT burtongerardo aziridinationof11pregnene320dioneusingphinses
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Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses

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