Mitra, S and Sarkar, R and Chakrabarty, A and Mukherjee, S (2022) Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp2)-H allylic alkylation of α,β-unsaturated carbonyls. In: Chemical Science, 13 (42). pp. 12491-12497.
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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.
| Item Type: | Journal Article |
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| Publication: | Chemical Science |
| Publisher: | Royal Society of Chemistry |
| Additional Information: | The copyright for this article belongs to the authors. |
| Keywords: | Alkylation; Allylation; Carbonyl compounds; Enantioselectivity; Iridium compounds; Transition metals; Unsaturated compounds, Allyl groups; Allylic alkylation; Enantioselective; High enantioselectivity; Kojic acid; Metal-catalyzed; Olefin complexes; Reaction catalyzed; Unsaturated carbonyl compounds; carbonyl, Catalysis |
| Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
| Date Deposited: | 03 Jan 2023 11:10 |
| Last Modified: | 03 Jan 2023 11:10 |
| URI: | https://eprints.iisc.ac.in/id/eprint/78672 |
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