Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1 av. de la Terrasse, Gif-sur-Yvette 91198 Cedex France.
Institut Lavoisier Versailles, UMR CNRS 8180, Université de Versailles-St-Quentin-en-Yvelines, Université Paris-Saclay, Versailles, France.
Org Lett. 2021 Jan 15;23(2):442-448. doi: 10.1021/acs.orglett.0c03947. Epub 2021 Jan 6.
Highly enantio- and regioselective (3 + 2) formal cycloaddition of β-substituted ene- and thioenecarbamates as well as cyclic enamides with quinone diimides catalyzed by a BINOL- and SPINOL-derived phosphoric acid is reported. A wide variety of 2,3-disubstituted 2-aminoindolines, including polycyclic ones, were prepared in generally high yields (up to 98%) with moderate to complete diastereoselectivities and in most cases excellent enantioselectivities (up to 99% ee).
本文报道了手性联萘酚和手性螺环二醇衍生的磷酸催化β-取代的烯基和硫代烯基碳酰胺以及环状烯酰胺与醌二亚胺的高对映选择性和区域选择性的（3 + 2）形式环加成反应。多种 2,3-二取代的 2-氨基吲哚啉，包括多环化合物，通常以较高的收率（高达 98%）、中等至完全的非对映选择性和大多数情况下优异的对映选择性（高达 99%ee）获得。
