Stereoselective Synthesis of Allylic Alcohols via Substrate Control on Asymmetric Lithiation

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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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: 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)

Creator: Linne, Yannick
Lücke, Daniel
Gerdes, Kjeld
Bajerke, Kevin
Kalesse, Markus

DOI: 10.1002/chem.202302699

URN: urn:nbn:de:101:1-2023112314050669005618

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:32 AM CEST

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Associated

Linne, Yannick
Lücke, Daniel
Gerdes, Kjeld
Bajerke, Kevin
Kalesse, Markus

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Sparteine-Free, Highly Stereoselective Construction of Complex Allylic Alcohols Using 1,2-Metallate Rearrangements

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Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols

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Stereoselective Synthesis of syn-Homoallylic Alcohols

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Manganese-catalyzed cyclopropanation of allylic alcohols with sulfones

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Ruthenium-Catalyzed Z-Selective Cross-Metathesis of Allylic Alcohols

Ruthenium-Catalyzed Z-Selective Cross-Metathesis of Allylic Alcohols

Cobalt‐Catalyzed Photo‐Semipinacol Rearrangement of Unactivated Allylic Alcohols

Cobalt‐Catalyzed Photo‐Semipinacol Rearrangement of Unactivated Allylic Alcohols

Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols

Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols

Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols

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Novel heterocycle syntheses from allylic alcohols and cyclobutanol derivatives

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Catalytic Asymmetric Synthesis of Chiral Allylic Esters

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Catalytic Asymmetric Allylic Alkylation with Vinylaluminum Reagents

Catalytic Asymmetric Allylic Alkylation with Vinylaluminum Reagents

Stereoselective Synthesis of Allylic Alcohols via Substrate Control on Asymmetric Lithiation

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Asymmetric α-Allylation of Aldehydes with Simple Allylic Alcohols

Asymmetric α-Allylation of Aldehydes with Simple Allylic Alcohols

Sparteine-Free, Highly Stereoselective Construction of Complex Allylic Alcohols Using 1,2-Metallate Rearrangements

Sparteine-Free, Highly Stereoselective Construction of Complex Allylic Alcohols Using 1,2-Metallate Rearrangements

Stereoselective Synthesis of syn-Homoallylic Alcohols

Stereoselective Synthesis of syn-Homoallylic Alcohols

Manganese-catalyzed cyclopropanation of allylic alcohols with sulfones

Manganese-catalyzed cyclopropanation of allylic alcohols with sulfones

Ruthenium-Catalyzed Z-Selective Cross-Metathesis of Allylic Alcohols

Ruthenium-Catalyzed Z-Selective Cross-Metathesis of Allylic Alcohols

Cobalt‐Catalyzed Photo‐Semipinacol Rearrangement of Unactivated Allylic Alcohols

Cobalt‐Catalyzed Photo‐Semipinacol Rearrangement of Unactivated Allylic Alcohols

Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols

Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols

Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols

Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols

Novel heterocycle syntheses from allylic alcohols and cyclobutanol derivatives

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Catalytic Asymmetric Synthesis of Chiral Allylic Esters

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Catalytic Asymmetric Allylic Alkylation with Vinylaluminum Reagents

Catalytic Asymmetric Allylic Alkylation with Vinylaluminum Reagents

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