Enantioselective Ammonium Ylide Mediated One‐Pot Synthesis of Highly Substituted γ ‐Butyrolactones
Abstract: An ammonium ylide mediated access towards trans‐β,γ‐disubstituted, all‐trans‐α,β,γ‐trisubstituted, and α,α,β,γ‐tetrasubstituted γ‐butyrolactones bearing a broad variety of functionalities was developed. Starting from widely accessible benzylidene Meldrum's acid derivatives and α‐bromo carbonyl compounds, γ‐butyrolactones were obtained in yields between 32–99% with up to excellent diastereoselectivities (>95:5) via a DABCO‐mediated [2+1] annulation. Utilization of enantiomerically pure cinchona alkaloid derivatives enables the first asymmetric ammonium ylide mediated method to provide (3R, 4R)‐β,γ‐disubstituted and (2R, 3R, 4R)‐α,β,γ‐trisubstituted γ‐butyrolactones in moderate to good yields with up to very good enantiomeric ratios (97:3). The scalability of the transformation was proven while determining the absolute configuration.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Enantioselective Ammonium Ylide Mediated One‐Pot Synthesis of Highly Substituted γ ‐Butyrolactones ; volume:362 ; number:12 ; year:2020 ; pages:2385-2396 ; extent:12
Advanced synthesis & catalysis ; 362, Heft 12 (2020), 2385-2396 (gesamt 12)
- Creator
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Drennhaus, Till
Öhler, Laura
Djalali, Saveh
Höfmann, Svenja
Müller, Clemens
Pietruszka, Jörg
Worgull, Dennis
- DOI
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10.1002/adsc.202000039
- URN
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urn:nbn:de:101:1-2022060512184055050613
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:24 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Drennhaus, Till
- Öhler, Laura
- Djalali, Saveh
- Höfmann, Svenja
- Müller, Clemens
- Pietruszka, Jörg
- Worgull, Dennis
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