Synthesis of Spirocyclic 1-Pyrrolines from Nitrones and Arynes through a Dearomative [3,3′]-Sigmatropic Rearrangement

被引：27

作者：

Alshreimi, Abdullah S. ^{[1
]}

Zhang, Guanqun ^{[1
]}

Reidl, Tyler W. ^{[1
]}

Pena, Ricardo L. ^{[1
]}

Koto, Nicholas-George ^{[1
]}

Islam, Shahidul M. ^{[1
]}

Wink, Donald J. ^{[1
]}

Anderson, Laura L. ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, 845 W Taylor St, Chicago, IL 60612 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 35期

基金：

美国国家科学基金会;

关键词：

dearomatization; dipolar cycloaddition; nitrones; spirocyclic pyrroline; sigmatropic rearrangement; CATALYTIC ASYMMETRIC DEAROMATIZATION; 1,3-DIPOLAR CYCLOADDITION; CLAISEN REARRANGEMENT; INTRAMOLECULAR DEAROMATIZATION; PHENOL DEAROMATIZATION; STEREOGENIC CENTERS; AMINO-ACIDS; DERIVATIVES; INDOLES; CONSTRUCTION;

D O I：

10.1002/anie.202004652

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A dearomative [3,3 ']-sigmatropic rearrangement that converts N-alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones has been developed by using the dipolar cycloaddition of an N-alkenylnitrone and an aryne to access these unusual transient rearrangement precursors. This cascade reaction affords spirocyclic pyrrolines that are inaccessible through dipolar cycloadditions of exocyclic cyclohexenones and provides a fundamentally new approach to novel spirocyclic pyrroline and pyrrolidine motifs that are common scaffolds in biologically-active molecules. Diastereoselective functionalization processes have also been explored to demonstrate the divergent synthetic utility of the unsaturated spirocyclic products.

引用

页码：15244 / 15248

页数：5

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