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

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

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-assiste...

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Veröffentlicht in:Journal of organic chemistry 2016-03, Vol.81 (6), p.2488-2493
Hauptverfasser: Yang, Bing, Shen, Minxing, Ji, Xiaozhou, Xu, Ziyan, Sun, Hao, Jiang, Bo, Li, Guigen
Format: Artikel
Sprache:eng
Schlagworte:
Acetates - chemistry
Acrylonitrile - chemistry
Catalysis
Hexanes - chemistry
Imines - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00049