He Hualing, Cao Yang, Xu Jun, Antilla Jon C
Institute for Molecular Design and Synthesis, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P.R. China.
Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening, Jiangsu Ocean University, Lianyungang 222005, P.R. China.
Org Lett. 2021 Apr 16;23(8):3010-3014. doi: 10.1021/acs.orglett.1c00699. Epub 2021 Apr 1.
A unique catalytic asymmetric C-7 Friedel-Crafts alkylation/-hemiacetalization cascade reaction of 4-aminoindoles with β,γ-unsaturated α-keto esters has been described. Using a chiral magnesium H-BINOL-derived bis(phosphate) complex as catalyst, the resulting functionalized 1,7-annulated indole scaffolds are obtained in high yields (up to 98%) and with good to excellent enantioselectivities (up to 99%) and diastereoselectivities (up to >20:1) under mild reaction conditions.
已报道了4-氨基吲哚与β,γ-不饱和α-酮酯的独特催化不对称C-7傅克烷基化/-半缩醛化串联反应。使用手性镁H-BINOL衍生的双(磷酸酯)配合物作为催化剂，在温和的反应条件下，以高产率(高达98%)、良好至优异的对映选择性(高达99%)和非对映选择性(高达>20:1)得到了官能化的1,7-稠合吲哚骨架。
