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手性路易斯碱催化的苯并稠合ε-内酯的不对称合成

Chiral Lewis Base-Catalysed Asymmetric Syntheses of Benzo-fused ϵ-Lactones.

作者信息

Stockhammer Lotte, Radetzky Maximilian, Khatoon Syeda Sadia, Bechmann Matthias, Waser Mario

机构信息

Institute of Organic Chemistry Johannes Kepler University Linz Altenbergerstrasse 69 4040 Linz Austria.

出版信息

European J Org Chem. 2023 Oct 16;26(39):e202300704. doi: 10.1002/ejoc.202300704. Epub 2023 Sep 18.

Abstract

We herein report a two-step protocol for the asymmetric synthesis of novel chiral benzofused ϵ-lactones starting from O-protected hydroxymethyl-para-quinone methides and activated aryl esters. By using chiral isothiourea Lewis base catalysts a broad variety of differently substituted products could be obtained in yields of around 50 % over both steps with high levels of enantioselectivities, albeit low diastereoselectivities only.

摘要

我们在此报告了一种两步法协议,用于从O-保护的羟甲基对醌甲基化物和活化的芳基酯开始不对称合成新型手性苯并稠合ε-内酯。通过使用手性异硫脲路易斯碱催化剂,可以在两步反应中以约50%的产率获得多种不同取代的产物,对映选择性高,尽管非对映选择性仅较低。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4bdb/11005097/5b0eaf5c66a9/EJOC-26-0-g002.jpg

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