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Chiral N‑Phosphonyl Imines for an Aza-Morita–Baylis–Hillman Reaction via Group-Assisted Purification (GAP) Chemistry

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posted on 2016-02-22, 00:00 authored by Bing Yang, Minxing Shen, Xiaozhou Ji, Ziyan Xu, Hao Sun, Bo Jiang, Guigen Li
Seventeen examples of aza-Morita–Baylis–Hillman (aza-MBH) adducts have been synthesized by reacting chiral N-phosphonyl imines with acrylonitrile in good to excellent yields (up to 96%) and high diastereoselectivity (up to 99:1 dr). The synthesis of these adducts followed the method of group-assisted purification (GAP) chemistry, in which the pure aza-MBH products were readily obtained by washing the crude products with cosolvents of hexane and ethyl acetate.