ChemInform Abstract: Synthesis of Enantiopure 1,4-Dioxanes, Morpholines, and Piperazines from the Reaction of Chiral 1,2-Diols, Amino Alcohols, and Diamines with Vinyl Selenones.

✍ Scribed by Luana Bagnoli; Catalina Scarponi; Maria Giovanna Rossi; Lorenzo Testaferri; Marcello Tiecco

• Publisher: John Wiley and Sons
• Year: 2011
• Weight: 57 KB
• Volume: 42
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.201121023

✦ Synopsis

Synthesis of Enantiopure 1,4-Dioxanes, Morpholines, and Piperazines from the Reaction of Chiral 1,2-Diols, Amino Alcohols, and Diamines with Vinyl Selenones. -The reaction of enantiopure diols, amino alcohols, or diamines with vinyl selenones in the presence of NaH represents a novel route to the title compounds. The configurations of the chiral carbon atoms in the products are unchanged with respect to those of the starting compounds. Thiomorpholine (XVII), oxazepine (XIX), and diazepine (XXI) are also prepared by this method in excellent yields. -(BAGNOLI*, L.;