Iridium-Catalyzed Enantioselective Alkene Hydroalkylation via a Heteroaryl-Directed Enolization-Decarboxylation Sequence.


Jing, Changcheng, Mao, Wenbin ORCID: 0000-0001-8746-1616 and Bower, John F ORCID: 0000-0002-7551-8221 (2023) Iridium-Catalyzed Enantioselective Alkene Hydroalkylation via a Heteroaryl-Directed Enolization-Decarboxylation Sequence. Journal of the American Chemical Society, 145 (44). pp. 23918-23924.

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Abstract

Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and α-olefins with diverse heteroaryl <i>tert</i>-butyl acetates occur with complete branched selectivity and very high enantioselectivity. The initial adducts undergo acid promoted decarboxylation in situ to provide alkylated heteroarenes possessing defined β-stereocenters. The processes are postulated to proceed via a stereodefined chiral Ir-enolate, which arises upon heteroarene directed enolization of the heteroaryl acetate precursor. The method can be classified as an enantioselective decarboxylative C(sp<sup>3</sup>)-C(sp<sup>3</sup>) cross-coupling.

Item Type: Article
Divisions: Faculty of Science and Engineering > School of Physical Sciences
Depositing User: Symplectic Admin
Date Deposited: 22 Nov 2023 15:23
Last Modified: 24 Nov 2023 14:04
DOI: 10.1021/jacs.3c10163
Open Access URL: https://doi.org/10.1021/jacs.3c10163
Related URLs:
URI: https://livrepository.liverpool.ac.uk/id/eprint/3176955
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