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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Aldol reactions between L-erythrulose derivatives and chiral alpha-amino and alpha-fluoro aldehydes: competition between Felkin-Anh and Cornforth transition states.

Both matched and mismatched diastereoselection have been observed in aldol reactions of a boron enolate of a protected L-erythrulose derivative with several chiral alpha-fluoro and alpha-amino aldehydes. Strict adherence to the Felkin-Anh model for the respective transition structures does not account satisfactorily for all the observed results, as previously observed in the case of alpha-oxygenated aldehydes. In some cases, only the Cornforth model provides a good explanation. The factors that influence this dichotomy are discussed and a general mechanistic model is proposed for aldol reactions with alpha-heteroatom-substituted aldehydes. Additional support for the model was obtained from density functional calculations.[1]

References

  1. Aldol reactions between L-erythrulose derivatives and chiral alpha-amino and alpha-fluoro aldehydes: competition between Felkin-Anh and Cornforth transition states. Díaz-Oltra, S., Carda, M., Murga, J., Falomir, E., Marco, J.A. Chemistry (2008) [Pubmed]
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