1393733-38-4Relevant academic research and scientific papers
Mechanistic insight into the anomalous syn-selectivity observed during the addition of allenylboronates to aromatic aldehydes
Sasaki, Yusuke,Sawamura, Masaya,Ito, Hajime
supporting information; experimental part, p. 1044 - 1046 (2011/12/05)
The reaction of enantioenriched allenylboronate 3a (98%ee) with benzaldehyde gave homopropargylic alcohol syn- and anti- 4b with anomalous syn addition selectivity (anti:syn = 29:71) and high ee (98% and 97%, respectively). The stereochemical outcome in terms of the absolute configuration shows that this reaction proceeds through a cyclic transition state. Density functional theoretical (DFT) calculations were carried out to elucidate the mechanism of this anomalous syn-selectivity.
