Lewis Acid Catalyzed Cyclopropane Ring-Opening-Cyclization Cascade Using Thioureas as a N,N-bisnucleophile: Synthesis of Bicyclic Furo-, Pyrano-, and Pyrrololactams via a Formal [4+1]-Addition

被引：1

作者：

Ratzenboeck, Andreas ^{[1
]}

Kobras, Manuel ^{[1
]}

Rustler, Anna ^{[1
]}

Reiser, Oliver ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, Univ Str 31, D-93053 Regensburg, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2024年 / 30卷 / 48期

关键词：

Cycloaddition; Cyclopropanes; Thiourea; Lewis acids; Furolactam; DONOR-ACCEPTOR CYCLOPROPANES; ENANTIOSELECTIVE SYNTHESIS; BOND INSERTION; DERIVATIVES;

D O I：

10.1002/chem.202401332

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fused bicyclic cyclopropanes were converted by Lewis acid-catalysis with thioureas to furo-, pyrano, and pyrrololactams with yields of up to 99 % and high diastereoselectivity. The formation of the title compounds, representing a formal [4+1]-cycloaddition to a donor-acceptor substituted cyclopropane, follows a cascade reaction involving SN1-type ring-opening addition and cyclization. Thiourea, being a cost-effective and odorless reagent, acts as an N,N-bis-nucleophile to generate bicyclic compounds containing an N-substituted gamma-lactam moiety.

引用

页数：4