1095607-33-2Relevant academic research and scientific papers
Aldol reactions between L-erythrulose derivatives and chiral α-amino and α-fluoro aldehydes: Competition between felkin-anh and cornforth transition states
Diaz-Oltra, Santiago,Carda, Miguel,Murga, Juan,Falomir, Eva,Marco, J. Alberto
scheme or table, p. 9240 - 9254 (2009/09/30)
Both matched and mismatched diastereoselection have been observed in aldol reactions of a boron enolate of a protected L-erythrulose derivative with several chiral α-fluoro and α-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 α-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 α-heteroatom-substituted aldehydes. Additional support for the model was obtained from density functional calculations.
