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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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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)
- Urheber
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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
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:24 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Drennhaus, Till
- Öhler, Laura
- Djalali, Saveh
- Höfmann, Svenja
- Müller, Clemens
- Pietruszka, Jörg
- Worgull, Dennis
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