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

Research output: Contribution to journalArticle

7 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 β-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 languageEnglish
Pages (from-to)6024-6035
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number25
DOIs
StatePublished - 2016

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