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Synthesis of Enantiopure 1,4‐Dioxanes, Morpholines, and Piperazines from the Reaction of Chiral 1,2‐Diols, Amino Alcohols, and Diamines with Vinyl Selenones
Author(s) -
Bagnoli Luana,
Scarponi Catalina,
Rossi Maria Giovanna,
Testaferri Lorenzo,
Tiecco Marcello
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002593
Subject(s) - enantiopure drug , chemistry , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis
Abstract The reactions of readily available vinyl selenones with enantiopure 1,2‐diols, N‐protected‐1,2‐aminoalcohols, and diamines gave substituted enantiopure 1,4‐dioxanes, morpholines, and piperazines, respectively, in good to excellent yields. The same procedure was extended to the synthesis of thiomorpholine, benzodiazepine, and benzoxazepine. The reactions proceeded in one pot, in the presence of base, through a simple and novel application of the Michael‐initiated, ring‐closure (MIRC) reactions. The formed heterocycles constitute a framework that is observed in a large number of pharmaceutical compounds.