Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 47, Pages 12907-12911Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406103
Keywords
homogeneous catalysis; olefination; phosphorus; Wittig reaction; ylide
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Funding
- Dublin City University (Career Start)
- Enterprise Ireland [CF/2011/1029]
- Australian Research Council [FT120100632]
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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 tert-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 E selectivity up to > 95:5, E/Z.
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