Chiral N-phosphonyl imine chemistry: asymmetric additions of malonate-derived enolates to chiral N-phosphonyl imines for the synthesis of β-aminomalonates
摘要:
Chiral N-phosphonyl imines attached by 1-naphthyl group were found to react with lithium malonate enolates smoothly to give chiral beta-aminomalonates. Good yields and excellent diastereoselectivity were achieved for sixteen examples. The chiral auxiliary Call be readily removed by treating with trifluoroacetic acid (TFA) to give free amino malonates. The absolute structure has been unambiguously determined by converting one of the products into an authentic sample. (c) 2009 Elsevier Ltd. All rights reserved.