Work

Divergent Catalysis: Catalytic Asymmetric [4+2] Cycloaddition of Palladium Enolates

Year: 2023

Type: article

Abstract: An asymmetric decarboxylative [4+2] cycloaddition from a catalytically generated chiral Pd enolate was developed, forging four contiguous stereocenters in a single transformation. This was achieved through a strategy termed divergent catalysis, wherein departure from a known catalytic cycle enables novel reactivity of a targeted intermediate prior to re-entry into the original cycle. Mechanistic studies including quantum mechanics calculations, Eyring analysis, and KIE studies offer insight into the reaction mechanism.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.3c02104

Authors: Kaylin N. Flesch, Alexander Q. Cusumano, Peng-Jui Chen, Christian Santiago Strong, Stephen R. Sardini, Yun E. Du, Michael D. Bartberger, William A. Goddard, Brian M. Stoltz

Institution: California Institute of Technology

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,000

Funders: National Science Foundation, California Institute of Technology, Heritage Medical Research Institute, National Institutes of Health, National Institute of General Medical Sciences, Division of Chemical, Bioengineering, Environmental, and Transport Systems

Awards: G5258027049, G5982874353, Collaborative Research: Modulating Single-Atom Catalytic Centers in Well-Defined Metal Oxide Nanocrystal Surfaces for Oxygen Evolution Reaction, The Synthesis of Bioactive Natural Products as a Driving Force for Discovery in Organic Chemistry, G910474268

OpenAlex ID: W4376602604

FWCI: 1.43

Cites: 32

Cited by: 14

Related to: 10