Synthesis of Enantiopure 1,4‐Dioxanes, Morpholines, and Piperazines from the Reaction of Chiral 1,2‐Diols, Amino Alcohols, and Diamines with Vinyl Selenones | Zendy

Bagnoli Luana | Zendy; Scarponi Catalina | Zendy; Rossi Maria Giovanna | Zendy; Testaferri Lorenzo | Zendy; Tiecco Marcello | Zendy

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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

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.

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