Work

Switchable Enantio- and Diastereoselective Michael Additions of β-Keto Amides to Nitroolefins: Crystallization-Based Inversion of Kinetic Stereocontrol

Year: 2024

Type: article

Abstract: Asymmetric catalytic reactions rely on chiral catalysts that induce highly ordered transition states capable of imparting stereoselectivity in the bond-forming step(s). Productive deviations from this paradigm are rare yet hold the potential for accessing different stereoisomers using the same catalyst. Here, we present an enantio- and diastereoselective Michael addition of β-keto amides to nitroolefin electrophiles proceeding via an unusual scenario where the kinetic diastereocontrol imparted by the catalyst may be overridden by crystallization to provide the complementary stereoisomer of the product.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c02617

Authors: William R. Cassels, Emily R. Sherman, Kaylah A. Longmore, Jeffrey S. Johnson

Institution: University of North Carolina at Chapel Hill

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences, Division of Chemistry