Stereoselective Synthesis of Allylic Alcohols via Substrate Control on Asymmetric Lithiation
Abstract: Allylic alcohols are a privileged motif in natural product synthesis and new methods that access them in a stereoselective fashion are highly sought after. Toward this goal, we found that chiral acetonide‐protected polyketide fragments performing the Hoppe–Matteson–Aggarwal rearrangement in the absence of sparteine with high yields and diastereoselectivities rendering this protocol a highly valuable alternative to the Nozaki–Hiyama–Takai–Kishi reaction. Various stereodyads and ‐triads were investigated to determine their substrate induction. The mostly strong inherent stereoinduction was attributed to a combination of steric and electronic effects.
- 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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Stereoselective Synthesis of Allylic Alcohols via Substrate Control on Asymmetric Lithiation ; day:22 ; month:11 ; year:2023 ; extent:8
Chemistry - a European journal ; (22.11.2023) (gesamt 8)
- Urheber
- DOI
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10.1002/chem.202302699
- URN
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urn:nbn:de:101:1-2023112314050669005618
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:32 MESZ
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Beteiligte
- Linne, Yannick
- Lücke, Daniel
- Gerdes, Kjeld
- Bajerke, Kevin
- Kalesse, Markus
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Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols
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