Enantioselective Intramolecular Iridium-Catalyzed Cyclopropanation of α-Carbonyl Sulfoxonium Ylides

Vidal, Lucas, Chen, Pan-Pan, Nicolas, Eva, Hackett, Andrew, Robertson, Craig M ORCID: 0000-0002-4789-7607, Houk, Kendall N and Aissa, Christophe ORCID: 0000-0003-0750-9435 (2022) Enantioselective Intramolecular Iridium-Catalyzed Cyclopropanation of α-Carbonyl Sulfoxonium Ylides. ORGANIC LETTERS, 24 (46). pp. 8503-8508.

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Official URL: http://dx.doi.org/10.1021/acs.orglett.2c03396

Abstract

Enantioselective cyclopropanation of α-carbonyl sulfoxonium ylides (SY) has so far been limited to addition/ring closure reactions on electron-poor olefins. Herein, we report the iridium-catalyzed intramolecular cyclopropanation of SY in the presence of a chiral diene in up to 96% yield and 98% enantioselectivity. Moreover, density functional theory calculations suggest that the <i>re</i> face of the olefin preferably attacks an iridium carbene intermediate in an asynchronous concerted step that is independent of the geometry of the olefin.

Item Type:	Article
Uncontrolled Keywords:	Iridium, Alkenes, Catalysis, Stereoisomerism
Depositing User:	Symplectic Admin
Date Deposited:	30 Nov 2022 11:54
Last Modified:	18 Oct 2023 12:17
DOI:	10.1021/acs.orglett.2c03396
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3166453