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

Bing Yang; Miming Shen; Xiaozhou Ji; Ziyan Xu; Hao Sun; Bo Jiang; Guigen Li

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

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	2488-2493
Journal	Journal of Organic Chemistry
State	Published - Mar 2016

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@article{90527e3d75df4fcfa06d29cf34ff2b0b,

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

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.",

author = "Bing Yang and Miming Shen and Xiaozhou Ji and Ziyan Xu and Hao Sun and Bo Jiang and Guigen Li",

year = "2016",

month = mar,

language = "English",

pages = "2488--2493",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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TY - JOUR

T1 - Chiral N-Phosphonyl Imines for an Aza-Morita-Baylis-Hillman Reaction via Group-Assisted Purification (GAP) Chemistry

AU - Yang, Bing

AU - Shen, Miming

AU - Ji, Xiaozhou

AU - Xu, Ziyan

AU - Sun, Hao

AU - Jiang, Bo

AU - Li, Guigen

PY - 2016/3

Y1 - 2016/3

N2 - 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.

AB - 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.

M3 - Article

SP - 2488

EP - 2493

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

ER -