Asymmetric synthesis of α-hydroxymethylphosphonates and phosphonic acids via hydrophosphonylation of aldehydes with chiral H-phosphonate

Diastereoselective hydrophosphonylation of aldehydes with a chiral H-phosphonate is described. High asymmetric inductions were obtained using a readily available TADDOL auxiliary. Subsequent, racemization-free removal of the chiral auxiliary led to the desired alpha-hydroxyphosphonic acids in very good yields and high enantiomeric purity as the (R)-enantiomers. (C) 2015 Elsevier Ltd. All rights reserved.