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Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols

Alessandra Casnati, Dawid Lichosyt, Bruno Lainer, Lukas Veth, Paweł Dydio

2021Organic Letters16 citationsDOIOpen Access PDF

Abstract

One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).

Topics & Concepts

ChemistryStereoselectivityIsomerizationAlkeneAllylic rearrangementNucleophileArylCatalysisMetathesisAlcoholOrganic chemistryCombinatorial chemistryPolymerizationAlkylPolymerSynthetic Organic Chemistry MethodsAsymmetric Hydrogenation and CatalysisChemical Synthesis and Analysis
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