A new approach that takes advantage of N-heterocyclic carbene/Lewis acid cooperative catalysis provides access to cis-1,3,4-trisubstituted cyclopentenes from enals and chalcone derivatives with high levels of diastereoselectivity and enantioselectivity. The presence of Ti(OiPr)4 as the Lewis acid allows for efficient substrate preorganization, which translates into high levels of diastereoselectivity. Additionally, we demonstrate the possibility of controlling the absolute stereochemistry of NHC-catalyzed reactions by employing a catalytic amount of a chiral Lewis acid as the unique source of optically active promoter.
|Original language||English (US)|
|Number of pages||3|
|Journal||Journal of the American Chemical Society|
|State||Published - Apr 21 2010|
ASJC Scopus subject areas
- Colloid and Surface Chemistry
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CCDC 793167: Experimental Crystal Structure Determination
Cardinal-David, B. (Creator), Raup, D. E. A. (Creator) & Scheidt, K. A. (Creator), Cambridge Crystallographic Data Centre, 2011
DOI: 10.5517/ccvmc1v, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccvmc1v&sid=DataCite