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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

URN to cite this document:
urn:nbn:de:bvb:355-epub-590381
DOI to cite this document:
10.5283/epub.59038
Ratzenböck, Andreas ; Kobras, Manuel ; Rustler, Anna ; Reiser, Oliver
[img]License: Creative Commons Attribution 4.0
PDF - Published Version
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Date of publication of this fulltext: 03 Sep 2024 04:21

This publication is part of the DEAL contract with Wiley.


Abstract

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, ...

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