Iridium-catalyzed enantioselective olefinic C(sp2)–H allylic alkylation

Rahul Sarkar; Santanu Mukherjee

doi:10.1039/D0SC06208A

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Iridium-catalyzed enantioselective olefinic C(sp²)–H allylic alkylation†

Rahul Sarkar

^a and Santanu Mukherjee

*^a

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* Corresponding authors

^a Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India
E-mail: sm@iisc.ac.in
Fax: +91-80-2360-0529
Tel: +91-80-2293-2850

Abstract

The first iridium-catalyzed enantioselective olefinic C(sp²)–H allylic alkylation is developed in cooperation with Lewis base catalysis. This reaction, catalyzed by cinchonidine and an in situ generated cyclometalated Ir(I)/phosphoramidite complex, makes use of the latent enolate character of an α,β-unsaturated carbonyl compound, namely coumalate ester, to introduce an allyl group at its α-position in a branched-selective manner in moderate to good yield with good to excellent enantioselectivities (up to 98 : 2 er).

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Article information

DOI: https://doi.org/10.1039/D0SC06208A
Article type: Edge Article
Submitted: 11 Nov 2020
Accepted: 14 Jan 2021
First published: 15 Jan 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2021,12, 3070-3075

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Iridium-catalyzed enantioselective olefinic C(sp²)–H allylic alkylation

R. Sarkar and S. Mukherjee, Chem. Sci., 2021, 12, 3070 DOI: 10.1039/D0SC06208A

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