Issue 9, 2022

Regiocontrolled synthesis of enantioenriched 2-substituted dehydropiperidines by stereospecific allyl–allyl cross-coupling of a chiral allylic boronate

Abstract

The palladium-catalyzed cross-coupling of an optically enriched dehydropiperidinyl boronate with cinnamyl carbonates was optimized to minimize stereochemical erosion. Although the coupling of two unsymmetrical allyl fragments may generate four possible regioisomers, the optimal procedure using (p-CF3C6H4)3P as the ligand affords linear 2-allylated 3,4-dehydropiperidines exclusively (>98 : 2 rr) with enantiospecificity up to 99%.

Graphical abstract: Regiocontrolled synthesis of enantioenriched 2-substituted dehydropiperidines by stereospecific allyl–allyl cross-coupling of a chiral allylic boronate

Supplementary files

Article information

Article type
Communication
Submitted
03 11 2021
Accepted
16 12 2021
First published
16 12 2021

Chem. Commun., 2022,58, 1370-1373

Regiocontrolled synthesis of enantioenriched 2-substituted dehydropiperidines by stereospecific allyl–allyl cross-coupling of a chiral allylic boronate

M. Estaitie and D. G. Hall, Chem. Commun., 2022, 58, 1370 DOI: 10.1039/D1CC06186K

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