Asymmetric aza-Morita-Baylis-Hillman reactions of chiral N-phosphonyl
imines with acrylates via GAP chemistry/technology

Bing Yang; Xiaozhou Ji; Yunsheng Xue; Haowei Zhang; Minxing Shen; Bo Jiang; Guigen Li

Asymmetric aza-Morita-Baylis-Hillman reactions of chiral N-phosphonyl imines with acrylates via GAP chemistry/technology

Bing Yang, Xiaozhou Ji, Yunsheng Xue, Haowei Zhang, Minxing Shen, Bo Jiang, Guigen Li

Chemistry and Biochemistry

Research output: Contribution to journal › Article

8 Scopus citations

Abstract

Chiral N-phosphonyl imines have been proven to be efficient electrophilic acceptors for asymmetric aza-Morita-Baylis-Hillman (aza-MBH) reactions with acrylates under convenient conditions. Thirty examples of beta-amino acrylates were generated in high yields (up to 99.4%) and diastereoselectivity (up to >99 : 1 dr) in an atom-economical fashion. The synthesis was proved to follow the GAP (group-assisted purification) chemistry, i.e., the pure products can be obtained simply by washing the crude products with hexane/ethyl acetate (v/v, 10/1) without the use of chromatography or recrystallization. DFT calculations were also conducted to support an asymmetric induction model accounting for high diastereoselectivity.

Original language	English
Pages (from-to)	6024-6035
Journal	Organic & Biomolecular Chemistry
State	Published - 2016

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title = "Asymmetric aza-Morita-Baylis-Hillman reactions of chiral N-phosphonyl imines with acrylates via GAP chemistry/technology",

abstract = "Chiral N-phosphonyl imines have been proven to be efficient electrophilic acceptors for asymmetric aza-Morita-Baylis-Hillman (aza-MBH) reactions with acrylates under convenient conditions. Thirty examples of beta-amino acrylates were generated in high yields (up to 99.4%) and diastereoselectivity (up to >99 : 1 dr) in an atom-economical fashion. The synthesis was proved to follow the GAP (group-assisted purification) chemistry, i.e., the pure products can be obtained simply by washing the crude products with hexane/ethyl acetate (v/v, 10/1) without the use of chromatography or recrystallization. DFT calculations were also conducted to support an asymmetric induction model accounting for high diastereoselectivity.",

author = "Bing Yang and Xiaozhou Ji and Yunsheng Xue and Haowei Zhang and Minxing Shen and Bo Jiang and Guigen Li",

note = "Funding Information: We would like to acknowledge the financial support from the National Natural Science Foundation of China (No. 21332005). We want to thank our co-worker Jing Li for his helpful discussions. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

language = "English",

pages = "6024--6035",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry (RSC)",

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TY - JOUR

T1 - Asymmetric aza-Morita-Baylis-Hillman reactions of chiral N-phosphonyl imines with acrylates via GAP chemistry/technology

AU - Yang, Bing

AU - Ji, Xiaozhou

AU - Xue, Yunsheng

AU - Zhang, Haowei

AU - Shen, Minxing

AU - Jiang, Bo

AU - Li, Guigen

N1 - Funding Information: We would like to acknowledge the financial support from the National Natural Science Foundation of China (No. 21332005). We want to thank our co-worker Jing Li for his helpful discussions. Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016

Y1 - 2016

N2 - Chiral N-phosphonyl imines have been proven to be efficient electrophilic acceptors for asymmetric aza-Morita-Baylis-Hillman (aza-MBH) reactions with acrylates under convenient conditions. Thirty examples of beta-amino acrylates were generated in high yields (up to 99.4%) and diastereoselectivity (up to >99 : 1 dr) in an atom-economical fashion. The synthesis was proved to follow the GAP (group-assisted purification) chemistry, i.e., the pure products can be obtained simply by washing the crude products with hexane/ethyl acetate (v/v, 10/1) without the use of chromatography or recrystallization. DFT calculations were also conducted to support an asymmetric induction model accounting for high diastereoselectivity.

AB - Chiral N-phosphonyl imines have been proven to be efficient electrophilic acceptors for asymmetric aza-Morita-Baylis-Hillman (aza-MBH) reactions with acrylates under convenient conditions. Thirty examples of beta-amino acrylates were generated in high yields (up to 99.4%) and diastereoselectivity (up to >99 : 1 dr) in an atom-economical fashion. The synthesis was proved to follow the GAP (group-assisted purification) chemistry, i.e., the pure products can be obtained simply by washing the crude products with hexane/ethyl acetate (v/v, 10/1) without the use of chromatography or recrystallization. DFT calculations were also conducted to support an asymmetric induction model accounting for high diastereoselectivity.

M3 - Article

AN - SCOPUS:84975833686

SN - 1477-0520

SP - 6024

EP - 6035

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

ER -

Asymmetric aza-Morita-Baylis-Hillman reactions of chiral N-phosphonyl imines with acrylates via GAP chemistry/technology

Abstract

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