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Org Lett. 2012 Oct 19;14(20):5310-3. doi: 10.1021/ol302493d. Epub 2012 Oct 10.

Explaining the disparate stereoselectivities of N-oxide catalyzed allylations and propargylations of aldehydes.

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  • 1Department of Chemistry, Texas A&M University, College Station, Texas 77843, USA


A simple electrostatic model explains the enhanced stereoselectivity of N-oxide catalyzed allylations compared to propargylations, which in turn explicates the dearth of stereoselective N-oxide propargylation catalysts. These results suggest that N-oxide catalysts that are effective for both allylations and propargylations can be designed by targeting inherently stereoselective ligand configurations and through the manipulation of distortion effects in the operative transition states.

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