A borane-mediated palladium-catalyzed reductive allylic alkylation of α,β-unsaturated carbonyl compounds†
Barry M.
Trost, 
*a
Zhijun
Zuo,
‡a
Johnathan E.
Schultz,
‡a
Nagaraju
Anugula
a
and
Katherine A.
Carr
a
*a
Zhijun
Zuo,
‡a
Johnathan E.
Schultz,
‡a
Nagaraju
Anugula
a
and
Katherine A.
Carr
a
Abstract
The development of the palladium-catalyzed allylic alkylation of in situ generated boron enolates via tandem 1,4-hydroboration is reported. Investigation of the reaction revealed insights into specific catalyst electronic features as well as a profound leaving group effect that proved crucial for achieving efficient allylic alkylation of ester enolates at room temperature and ultimately a highly preparatively useful synthesis of notoriously challenging acyclic all-carbon quaternary stereocenters. The method demonstrates boron enolates as viable pro-nucleophiles in transition-metal catalyzed allylic alkylation, potentially opening up further transformations outside their traditional use.
- This article is part of the themed collection: Celebrating our 2020 Prize and Award winners
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