Issue 42, 2022

Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp2)–H allylic alkylation of α,β-unsaturated carbonyls

Abstract

Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp2)–H allylic alkylation of kojic acid and structurally related α,β-unsaturated carbonyl compounds is developed. This reaction, catalyzed by an Ir(I)/(P,olefin) complex, utilizes the nucleophilic character of α-hydroxy α,β-unsaturated carbonyls, to introduce an allyl group at its β-position in a branched-selective manner in good to excellent yield with uniformly high enantioselectivity (up to >99.9 : 0.1 er). To the best of our knowledge, this report represents the first example of the use of kojic acid in a transition metal catalyzed highly enantioselective transformation.

Graphical abstract: Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp2)–H allylic alkylation of α,β-unsaturated carbonyls

Supplementary files

Article information

Article type
Edge Article
Submitted
15 Jul 2022
Accepted
12 Oct 2022
First published
13 Oct 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 12491-12497

Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp2)–H allylic alkylation of α,β-unsaturated carbonyls

S. Mitra, R. Sarkar, A. Chakrabarty and S. Mukherjee, Chem. Sci., 2022, 13, 12491 DOI: 10.1039/D2SC03966D

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