Catalytic Wittig Reactions of Semi‐ and Nonstabilized Ylides Enabled by Ylide Tuning1. (22nd September 2014)

• Record Type: Journal Article
• Authors: Coyle, Emma E.; Doonan, Bryan J.; Holohan, Andrew J.; Walsh, Killian A.; Lavigne, Florie; Krenske, Elizabeth H.; O'Brien, Christopher J.
• Is Part Of: Angewandte Chemie. Volume 126:Number 47(2014)
• Page Start: 13121
• Page End: 13125
• Publication Date: 2014-09-22
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201406103
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The first examples of catalytic Wittig reactions with semistabilized and nonstabilized ylides are reported. These reactions were enabled by utilization of a masked base, sodium <italic>tert</italic>‐butyl carbonate, and/or ylide tuning. The acidity of the ylide‐forming proton was tuned by varying the electron density at the phosphorus center in the precatalyst, thus facilitating the use of relatively mild bases. Steric modification of the precatalyst structure resulted in significant enhancement of <italic>E</italic> selectivity up to &gt;95:5, <italic>E</italic>/<italic>Z</italic>.</p> </abstract>