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 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.
authors.affiliation: Institute of Chemistry and BioMedical Sciences and School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. China. guigen.li@ttu.edu.
authors.forename: Bing
authors.initials: B
authors.lastname: Yang
authors.forename: Xiaozhou
authors.initials: X
authors.lastname: Ji
authors.forename: Yunsheng
authors.initials: Y
authors.lastname: Xue
authors.forename: Haowei
authors.initials: H
authors.lastname: Zhang
authors.forename: Minxing
authors.initials: M
authors.lastname: Shen
authors.forename: Bo
authors.initials: B
authors.lastname: Jiang
authors.forename: Guigen
authors.initials: G
authors.lastname: Li