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. 2007 Mar 15;9(6):1013-6.
doi: 10.1021/ol0630494. Epub 2007 Feb 13.

N-heterocyclic carbene-catalyzed Mukaiyama aldol reactions

Jinhua J Song  1 , Zhulin Tan, Jonathan T Reeves, Nathan K Yee, Chris H Senanayake
Affiliations

N-heterocyclic carbene-catalyzed Mukaiyama aldol reactions

Jinhua J Song et al. Org Lett. .

Abstract

N-Heterocyclic carbenes were shown to be highly effective catalysts to promote Mukaiyama aldol reactions. In the presence of only 0.5 mol % of N-heterocyclic carbene (5), various aldehydes and 2,2,2-trifluoroacetophenone underwent Mukaiyama aldol reactions in THF with trimethylsilyl ketene acetal (2) at 23 degrees C as well as with trimethylsilyl enol ether (7) at 0 degrees C to afford aldol adducts in good yields. These conditions are extremely mild and operationally simple and tolerate various functional groups. [reaction: see text]

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