Sequential Photochemical and Prins Reactions for the Diastereo-selective Synthesis of Tricyclic Scaffolds

被引：21

作者：

Donnelly, Bethan L. ^{[1
]}

Elliott, Luke D. ^{[1
]}

Willis, Christine L. ^{[1
]}

Booker-Milburn, Kevin I. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 27期

基金：

英国工程与自然科学研究理事会;

关键词：

cyclobutene; fluorination; photochemistry; Prins cyclization; Ritter reaction; RITTER REACTION SEQUENCE; FLOW REACTOR; ONE-POT; 4-AMIDOTETRAHYDROPYRANS; 3-COMPONENT;

D O I：

10.1002/anie.201903488

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclobutene alcohols undergo Prins cyclisations to generate single diastereomers of novel tricyclic heterocycles with five contiguous stereocentres. The reaction times are significantly shorter (ca. 15 min) than with traditional alkene substrates. Stereoselective aza-Prins cyclisations of cyclobutene amine derivatives give fused aza-heterocyclic scaffolds. Computational studies provide insight into the observed stereocontrol. The modular approach is flexible, enabling the introduction of a variety of functional groups (including amides, nitriles, alkynes, and arenes) into the sp3-rich heterocyclic scaffolds.

引用

页码：9095 / 9098

页数：4

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