4.8 Article

NHC-Catalyzed/Titanium(IV)-Mediated Highly Diastereo- and Enantioselective Dimerization of Enals

Journal

ORGANIC LETTERS
Volume 13, Issue 5, Pages 1068-1071

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol103112v

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Funding

  1. NIH [RO1-NIGMS]
  2. Amgen
  3. AstraZeneca
  4. GlaxoSmithKline
  5. GAANN
  6. FQRNT (Fonds Quebecois de la Recherche sur la Nature et les Technologies)
  7. U.S. Department of Energy [DE-AC02-06CH11357]
  8. Michigan Economic Development Corp. [085P1000817]

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An NHC-catalyzed, diastereo- and enantioselective dimerization of enals has been developed. The use of Ti(Oi-Pr)(4) is a key element for the reactivity and selectivity of this process. The cyclopentenes are obtained with high levels of diastereo- and enantioselectivity and their synthetic utility is demonstrated by functionalization of the product alkene.

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