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. 2010 Apr 21;132(15):5345-7.
doi: 10.1021/ja910666n.

Cooperative N-heterocyclic carbene/Lewis acid catalysis for highly stereoselective annulation reactions with homoenolates

Benoit Cardinal-David  1 , Dustin E A Raup, Karl A Scheidt
Affiliations

Cooperative N-heterocyclic carbene/Lewis acid catalysis for highly stereoselective annulation reactions with homoenolates

Benoit Cardinal-David et al. J Am Chem Soc. .

Abstract

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.

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Figures

Scheme 1
Scheme 1
Proposed Catalytic Pathway
See this image and copyright information in PMC

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