Divergent synthesis of δ-valerolactones and furanones palladium or copper-catalyzed α-hydroxycyclopropanol ring opening cyclizations

Cyclopropanols are versatile starting materials which can undergo various ring opening reactions due to their intrisic ring strain. Herein, we report two transition metal-catalyzed α-hydroxycyclopropanol ring opening cyclizations to divergently transform the same α-hydroxycyclopropanol substrate int...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2024-09, Vol.6 (74), p.1112-1115
Hauptverfasser: de Andrade Horn, Pedro, Collins, Michael J. E, Gudeman, Cyrus C, Fresh, Alexandra A, Dai, Mingji
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container_issue 74
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container_title Chemical communications (Cambridge, England)
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creator de Andrade Horn, Pedro
Collins, Michael J. E
Gudeman, Cyrus C
Fresh, Alexandra A
Dai, Mingji
description Cyclopropanols are versatile starting materials which can undergo various ring opening reactions due to their intrisic ring strain. Herein, we report two transition metal-catalyzed α-hydroxycyclopropanol ring opening cyclizations to divergently transform the same α-hydroxycyclopropanol substrate into two different products of enhanced value. One is a palladium-catalyzed α-hydroxycyclopropanol ring opening carbonylative lactonization to synthesize δ-valerolactones. The other one is a copper-catalyzed α-hydroxycyclopropanol ring opening cyclization to access furanones. Divergent approaches were developed to synthesize δ-valerolactones or furanones via a palladium or copper-catalyzed α-hydroxycyclopropanol ring opening cyclizations, respectively.
doi_str_mv 10.1039/d4cc03255a
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title Divergent synthesis of δ-valerolactones and furanones palladium or copper-catalyzed α-hydroxycyclopropanol ring opening cyclizations
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