Premium
Practical Syntheses of Enantiomerically Pure N ‐Acetylbenzhydrylamines
Author(s) -
Castagnolo Daniele,
Giorgi Gianluca,
Spinosa Raffaella,
Corelli Federico,
Botta Maurizio
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700193
Subject(s) - chemistry , bifonazole , alkyne , alkene , enantiomer , metathesis , combinatorial chemistry , salt metathesis reaction , organic chemistry , methylene , diene , aryl , antifungal , catalysis , medicine , polymer , natural rubber , dermatology , polymerization , alkyl
Abstract Two practical routes for the synthesis of benzhydrylamine derivatives in enantiomerically pure form have been developed. N ‐Acetylbenzhydrylamines can be synthesised in few steps and good yields starting from 1‐aryl‐1‐propargylamines. The key steps are represented by the alkene‐alkyne cross metathesis reaction and alkyne–diene methylene‐free tandem‐metathesis reaction; these reactions have been performed under microwave irradiation in a few minutes and high yields. N ‐Acetylbenzhydrylamines have been also converted in both enantiomers of the antifungal agent bifonazole, emphasizing the importance of these compounds as scaffolds for the synthesis of biologically active compounds in enatiopure form.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)