通过手性磷酸催化吲哚与5-取代羟基丁内酰胺的傅克烷基化反应对四取代碳立体中心进行对映选择性构建。

Enantioselective Construction of Tetrasubstituted Carbon Stereocenters via Chiral Phosphoric Acid-Catalyzed Friedel-Craft Alkylation of Indoles with 5-Substituted Hydroxybutyrolactams.

作者信息

Saidah Milane, Mardjan Muhammad Idham Darussalam, Masson Géraldine, Parrain Jean-Luc, Commeiras Laurent

机构信息

Aix Marseille University, CNRS, Centrale Marseille, iSm2, 13397 Marseille, France.

Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.

出版信息

Org Lett. 2022 Jul 29;24(29):5298-5303. doi: 10.1021/acs.orglett.2c01898. Epub 2022 Jul 14.

DOI:10.1021/acs.orglett.2c01898

PMID:35834747

Abstract

The first intermolecular organocatalytic enantioselective addition of indoles to prochiral 5-membered cyclic -acyliminium ions, generated from 5-hydroxy-α,β-unsaturated pyrrolidin-2-ones, is reported hereinafter. The reaction proceeds smoothly with a range of 5-hydroxy-5-substituted-α,β-unsaturated pyrrolidin-2-ones and indoles using BINOL-derived phosphoric acid catalyst to afford α,β-unsaturated lactams embedding a tetrasubstituted stereogenic center in high yields and enantioselectivities.

摘要

下文报道了首例分子间有机催化吲哚对前手性五元环 - 酰亚胺离子的对映选择性加成反应，该前手性五元环 - 酰亚胺离子由5-羟基-α,β-不饱和吡咯烷-2-酮生成。使用BINOL衍生的磷酸催化剂，一系列5-羟基-5-取代-α,β-不饱和吡咯烷-2-酮与吲哚的反应顺利进行，以高收率和对映选择性得到嵌入四取代立体中心的α,β-不饱和内酰胺。