Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines
Two practical routes for the synthesis of benzhydrylamine derivs. in enantiomerically pure form have been developed. Enzymic kinetic resoln. of racemic N-acetylpropargylamines RC6H4CH(NHAc)C≡CH with Candida antarctica Lipase B gave access to (R)-RC6H4CH(NHAc)C≡CH (1a-e; R = H, 4-F, 4-Cl, 3-F, 3-Me),...
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ftunivsiena:oai:usiena-air.unisi.it:11365/27625 2024-04-14T08:01:11+00:00 Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines Castagnolo, Daniele Spinosa, Raffaella GIORGI, GIANLUCA CORELLI, FEDERICO BOTTA, MAURIZIO Castagnolo, Daniele Giorgi, Gianluca Spinosa, Raffaella Corelli, Federico Botta, Maurizio 2007 STAMPA http://hdl.handle.net/11365/27625 https://doi.org/10.1002/ejoc.200700193 eng eng info:eu-repo/semantics/altIdentifier/wos/WOS:000248558500009 issue:22 firstpage:3676 lastpage:3686 numberofpages:11 journal:EUROPEAN JOURNAL OF ORGANIC CHEMISTRY http://hdl.handle.net/11365/27625 doi:10.1002/ejoc.200700193 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-34547684049 info:eu-repo/semantics/closedAccess info:eu-repo/semantics/article 2007 ftunivsiena https://doi.org/10.1002/ejoc.200700193 2024-03-21T15:56:46Z Two practical routes for the synthesis of benzhydrylamine derivs. in enantiomerically pure form have been developed. Enzymic kinetic resoln. of racemic N-acetylpropargylamines RC6H4CH(NHAc)C≡CH with Candida antarctica Lipase B gave access to (R)-RC6H4CH(NHAc)C≡CH (1a-e; R = H, 4-F, 4-Cl, 3-F, 3-Me), which were subjected to alkyne-alkene cross-metathesis catalyzed by Grubbs' 2nd generation catalyst, yielding (R,E/Z)-RC6H4CH(NHAc)C(:CH2)CH:CHR1 (2a-j; same R, R1 = H, OEt, OAc, TMS, CN, 3-MeOC6H4). (E)-Isomers 2 undergo Diels-Alder cycloaddn., giving α-(1-cyclohexenyl)benzylamines (R)-RC6H4CH(NHAc)(1-C6H7-4-X-3-OEt) (3d-e; R = H, X = CHO, COMe), heterodienophiles (Et glyoxalate, DEAD) gave dihydropyran and tetrahydropyridazine derivs., 4-[PhCH(NHAc)]-2-(CO2Et)-6-EtOC5H5O (3g) and 4-[PhCH(NHAc)]-1,2-(CO2Et)2-6-EtOC4H4N2 (3f), resp. N-Acetylbenzhydrylamine 3e was converted in both enantiomers of the fungicide bifonazole in multi-step procedure, emphasizing the importance of these compds. as scaffolds for the synthesis of biol. active compds. in enantiopure form. Article in Journal/Newspaper Antarc* Antarctica Università degli Studi di Siena: USiena air European Journal of Organic Chemistry 2007 22 3676 3686 |
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Università degli Studi di Siena: USiena air |
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ftunivsiena |
language |
English |
description |
Two practical routes for the synthesis of benzhydrylamine derivs. in enantiomerically pure form have been developed. Enzymic kinetic resoln. of racemic N-acetylpropargylamines RC6H4CH(NHAc)C≡CH with Candida antarctica Lipase B gave access to (R)-RC6H4CH(NHAc)C≡CH (1a-e; R = H, 4-F, 4-Cl, 3-F, 3-Me), which were subjected to alkyne-alkene cross-metathesis catalyzed by Grubbs' 2nd generation catalyst, yielding (R,E/Z)-RC6H4CH(NHAc)C(:CH2)CH:CHR1 (2a-j; same R, R1 = H, OEt, OAc, TMS, CN, 3-MeOC6H4). (E)-Isomers 2 undergo Diels-Alder cycloaddn., giving α-(1-cyclohexenyl)benzylamines (R)-RC6H4CH(NHAc)(1-C6H7-4-X-3-OEt) (3d-e; R = H, X = CHO, COMe), heterodienophiles (Et glyoxalate, DEAD) gave dihydropyran and tetrahydropyridazine derivs., 4-[PhCH(NHAc)]-2-(CO2Et)-6-EtOC5H5O (3g) and 4-[PhCH(NHAc)]-1,2-(CO2Et)2-6-EtOC4H4N2 (3f), resp. N-Acetylbenzhydrylamine 3e was converted in both enantiomers of the fungicide bifonazole in multi-step procedure, emphasizing the importance of these compds. as scaffolds for the synthesis of biol. active compds. in enantiopure form. |
author2 |
Castagnolo, Daniele Giorgi, Gianluca Spinosa, Raffaella Corelli, Federico Botta, Maurizio |
format |
Article in Journal/Newspaper |
author |
Castagnolo, Daniele Spinosa, Raffaella GIORGI, GIANLUCA CORELLI, FEDERICO BOTTA, MAURIZIO |
spellingShingle |
Castagnolo, Daniele Spinosa, Raffaella GIORGI, GIANLUCA CORELLI, FEDERICO BOTTA, MAURIZIO Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines |
author_facet |
Castagnolo, Daniele Spinosa, Raffaella GIORGI, GIANLUCA CORELLI, FEDERICO BOTTA, MAURIZIO |
author_sort |
Castagnolo, Daniele |
title |
Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines |
title_short |
Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines |
title_full |
Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines |
title_fullStr |
Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines |
title_full_unstemmed |
Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines |
title_sort |
practical syntheses of enantiomerically pure n-acetylbenzhydrylamines |
publishDate |
2007 |
url |
http://hdl.handle.net/11365/27625 https://doi.org/10.1002/ejoc.200700193 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/wos/WOS:000248558500009 issue:22 firstpage:3676 lastpage:3686 numberofpages:11 journal:EUROPEAN JOURNAL OF ORGANIC CHEMISTRY http://hdl.handle.net/11365/27625 doi:10.1002/ejoc.200700193 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-34547684049 |
op_rights |
info:eu-repo/semantics/closedAccess |
op_doi |
https://doi.org/10.1002/ejoc.200700193 |
container_title |
European Journal of Organic Chemistry |
container_volume |
2007 |
container_issue |
22 |
container_start_page |
3676 |
op_container_end_page |
3686 |
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1796307871334400000 |