Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes)

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Abstract: Enantiomerically enriched crown ethers (CE) exhibit strong asymmetric induction in phase transfer catalysis, supramolecular catalysis and molecular recognition processes. Traditional methods have often been used to access these valuable compounds, which limit their diversity and consequently their applicability. Herein, a practical catalytic method is described for the gram scale synthesis of a class of chiral CEs (aza‐crown ethers; ACEs) using Rh‐catalyzed hydroamination of bis (allenes) with diamines. Using this approach, a wide range of chiral vinyl functionalized CEs with ring sizes ranging from 12 to 36 have been successfully prepared in high yields of up to 92 %, dr of up to >20: 1 and er of up to >99: 1. These vinyl substituted CEs allow for further diversification giving facile access to various CE derivatives as well as to their three‐dimensional analogues using ring‐closing metathesis. Some of these chiral CEs themselves display high potential for use in asymmetric catalysis.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes) ; day:28 ; month:02 ; year:2024 ; extent:12
Angewandte Chemie ; (28.02.2024) (gesamt 12)

Urheber
Panahi, Farhad
Breit, Bernhard

DOI
10.1002/ange.202317981
URN
urn:nbn:de:101:1-2024022814284583418315
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
14.08.2025, 10:58 MESZ

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