Diastereoselective Synthesis of Tetrahydrofurans from Aryl 3-Chloropropylsulfoxides and Aldehydes‡

Z Komsta, M Barbasiewicz…

Index: Komsta, Zofia; Barbasiewicz, Michal; Makosza, Mieczyslaw Journal of Organic Chemistry, 2010 , vol. 75, # 10 p. 3251 - 3259

Full Text: HTML

Citation Number: 6

Abstract

Carbanions of aryl 3-chloropropylsulfoxides react with nonenolizable aldehydes to give 2, 3- disubstituted tetrahydrofurans. Deprotonation of the sulfoxides carried out in the presence of aldehydes results in the addition of the carbanions to the carbonyl group of the aldehydes, followed by 1, 5-intramolecular substitution of the resulting aldol-type anion to produce the tetrahydrofuran ring. The 2-aryl and 3-arylsulfinyl substituents are always in trans relation, ...

Related Articles:

A new and convenient synthetic method for cyclopropyl phenyl sulfides

[Tanaka, Kazuhiko; Uneme, Hideki; Matsui, Shuichi; Kaji, Aritsune Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 9 p. 2965 - 2972]

Synthesis and QSAR studies on hypotensive 1-[3-(4-substituted phenylthio) propyl]-4-(substituted phenyl) piperazines

[Saxena, Anil K.; Rao, Jyoti; Chakrabarty, Ruchika; Saxena, Mridula; Srimal Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 6 p. 1708 - 1712]

More Articles...