(Diphenoxyphosphoryl)methyl p-tolyl sulfoxide: A new reagent for Z-selective synthesis of racemic and optically active vinyl sulfoxides. (3rd March 2016)

• Record Type: Journal Article
• Authors: Midura, Wanda H.; Ewas, Ashraf M. Mohamed; Mikołajczyk, Marian
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 191:Number 3(2016)
• Page Start: 535
• Page End: 540
• Publication Date: 2016-03-03
• Subjects: Chiral (diphenoxyphosphoryl)methyl p-tolyl sulfoxide -- vinyl sulfoxides -- Horner reaction -- Z-selectivity; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2015.1114489
• Languages: English
• ISSNs: 1042-6507

Abstract

GRAPHICAL ABSTRACT: ABSTRACT: Racemic and optically active (+)-( S )-(diphenoxyphosphoryl)methyl p -tolyl sulfoxide were prepared and used as Horner olefination reagents. Their reaction with aromatic and aliphatic aldehydes afforded the corresponding racemic and enantiomeric α, β-unsaturated sulfoxides with moderate to high Z -selectivity. The E / Z ratio was found to be dependent on the structure of aldehyde, nature of base, reaction conditions, and addition of 18-crown-6.