Issue 44, 2018

Asymmetric synthesis of α-trifluoromethoxy ketones with a tetrasubstituted α-stereogenic centre via the palladium-catalyzed decarboxylative allylic alkylation of allyl enol carbonates

Abstract

The palladium-catalyzed asymmetric decarboxylative allylic alkylation of trifluoromethoxy allyl enol carbonates afforded enantioenriched α-trifluoromethoxy allyl ketones that feature a tetrasubstituted α-stereogenic center in excellent yield and high enantioselectivity. The method was further extended to the asymmetric synthesis of α-difluoromethoxy and α-methoxy allyl ketones, which proceeded under similar catalytic conditions.

Graphical abstract: Asymmetric synthesis of α-trifluoromethoxy ketones with a tetrasubstituted α-stereogenic centre via the palladium-catalyzed decarboxylative allylic alkylation of allyl enol carbonates

Supplementary files

Article information

Article type
Communication
Submitted
18 Apr 2018
Accepted
03 May 2018
First published
04 May 2018

Chem. Commun., 2018,54, 5522-5525

Asymmetric synthesis of α-trifluoromethoxy ketones with a tetrasubstituted α-stereogenic centre via the palladium-catalyzed decarboxylative allylic alkylation of allyl enol carbonates

H. Kondo, M. Maeno, K. Hirano and N. Shibata, Chem. Commun., 2018, 54, 5522 DOI: 10.1039/C8CC03131B

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