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

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...

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Published in:Organic letters 2021-05, Vol.23 (9), p.3502-3506
Main Authors: Casnati, Alessandra, Lichosyt, Dawid, Lainer, Bruno, Veth, Lukas, Dydio, Paweł
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Language:English
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Catalysis
Chemical Sciences
Organic chemistry
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cited_by cdi_FETCH-LOGICAL-a424t-f0214e7d74318dbd123f936b58ba67c767b9717823b6dda00b5f34c7412bd2b63
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container_title Organic letters
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creator Casnati, Alessandra
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description 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).
doi_str_mv 10.1021/acs.orglett.1c00939
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subjects Catalysis
Chemical Sciences
Organic chemistry
title Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols
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