1010708-47-0Relevant articles and documents
A practical synthesis of syn- and anti-α,β-dihydroxyphosphinates via diastereoselective reduction of α-phosphinoyl ketones
Rojas-Cabrera, Haydee,Hernandez-Perez, Julio M.,Ho, Minhhuy,Hernandez-Fernandez, Eugenio,Ordonez, Mario
, p. 161 - 166 (2008)
Reduction of β-keto-diphenylphosphine oxide (S)-4 derived from (S)-mandelic acid with NaBH4 in methanol at -78 °C gave the anti-3-diphenylphosphinoyl-1,2-diol 6, whereas the reduction of (S)-4 with Zn(BH4)2 in THF at -78 °C afforded the syn-1,2-diol 5, both in high yield and excellent diastereoselectivity. This procedure represents a new approach to the diastereoselective synthesis of diphenylphosphinoyl diols and an example of highly diastereoselective 1,2-induction. A theoretical model to explain the direction and degree of asymmetric induction is proposed.