Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/5360
Title: Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines
Authors: Castagnolo, Daniele
Giorgi, Gianluca 
Spinosa, Raffaella
Corelli, Federico 
Botta, Maurizio 
Issue Date: 2007
Project: None 
Journal: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Abstract: 
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.
Description: 
44152
URI: http://hdl.handle.net/20.500.12779/5360
ISSN: 1434-193X
DOI: 10.1002/ejoc.200700193
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