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

Bing Yang, Minxing Shen, Xiaozhou Ji, Ziyan Xu, Hao Sun, Bo Jiang, Guigen Li

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)2488-2493
Number of pages6
JournalJournal of Organic Chemistry
Volume81
Issue number6
DOIs
StatePublished - Mar 18 2016

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