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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Bibliographic Details
Published in:Organic letters 2021-05, Vol.23 (9), p.3502-3506
Main Authors: Casnati, Alessandra, Lichosyt, Dawid, Lainer, Bruno, Veth, Lukas, Dydio, Paweł
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
Organic chemistry
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Summary: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).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00939