Archive for September 30th, 2018

Organocatalytic cyclopropanation of an enal: Transition state models for stereoselection.

Sunday, September 30th, 2018

Here is the concluding part of my exploration of a recently published laboratory experiment for undergraduate students.[cite]10.1021/acs.jchemed.7b00566[/cite] I had previously outlined a possible mechanistic route, identifying TS3 (below) as the first transition state in which C-C bond formation creates two chiral centres. This is followed by a lower energy TS4 where the final stereocentre is formed, accompanied by inversion of configuration of one of the previously formed centres (red below). Now I explore what transition state calculations have to say about the absolute configurations of the final stereocentres in the carbaldehyde product.

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