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

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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, ...