Enantioselective One-Pot Synthesis of Cyclopropane-Fused Tetrahydroquinolines via a Ru-Catalyzed Intramolecular Cyclopropanation

A highly enantioselective one-pot synthesis of cyclopropane-fused tetrahydroquinolines bearing carbonyl functionalities, which are difficult to synthesize using conventional methods, is reported. Employing readily accessible alkene-tethered anthranilaldehydes, hydrazone formation and subsequent Ru-c...

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Veröffentlicht in:	Organic letters 2024-08, Vol.26 (30), p.6502-6506
Hauptverfasser:	Tsujihara, Tetsuya, Nishino, Koki, Miura, Wakaba, Chiba, Ayumi, Hayashi, Wakana, Yoshida, Chika, Takehara, Tsunayoshi, Suzuki, Takeyuki, Kawano, Tomikazu
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Sprache:	eng
Schlagworte:	alkenes enantioselectivity hydrazones synthesis
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creator	Tsujihara, Tetsuya Nishino, Koki Miura, Wakaba Chiba, Ayumi Hayashi, Wakana Yoshida, Chika Takehara, Tsunayoshi Suzuki, Takeyuki Kawano, Tomikazu
description	A highly enantioselective one-pot synthesis of cyclopropane-fused tetrahydroquinolines bearing carbonyl functionalities, which are difficult to synthesize using conventional methods, is reported. Employing readily accessible alkene-tethered anthranilaldehydes, hydrazone formation and subsequent Ru-catalyzed intramolecular cyclopropanation furnish the desired products in ≤87% yield and ≤95% ee under mild conditions. Various anthranilaldehydes, functionalized alkenes, and N-aryl sulfonyl groups are tolerated, and a series of synthetic transformations were conducted to demonstrate the practical utility.
doi_str_mv	10.1021/acs.orglett.4c02416
format	Article
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Lett</addtitle><date>2024-08-02</date><risdate>2024</risdate><volume>26</volume><issue>30</issue><spage>6502</spage><epage>6506</epage><pages>6502-6506</pages><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>A highly enantioselective one-pot synthesis of cyclopropane-fused tetrahydroquinolines bearing carbonyl functionalities, which are difficult to synthesize using conventional methods, is reported. Employing readily accessible alkene-tethered anthranilaldehydes, hydrazone formation and subsequent Ru-catalyzed intramolecular cyclopropanation furnish the desired products in ≤87% yield and ≤95% ee under mild conditions. 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subjects	alkenes enantioselectivity hydrazones synthesis
title	Enantioselective One-Pot Synthesis of Cyclopropane-Fused Tetrahydroquinolines via a Ru-Catalyzed Intramolecular Cyclopropanation
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