Work

Synthesis and Application of Chiral 2-Amido and 1-Phenyl-2-amido Dienes in Diels–Alder Reactions to Access Chiral Cyclic Ketones

Year: 2024

Type: article

Abstract: The preparation of a focused library of chiral 2-amido and 2-amido-1-phenyl-1,3-dienes from a range of chiral oxazolidinones using palladium-catalysis is reported. This palladium-catalyzed carbon-nitrogen bond-forming reaction provides the corresponding chiral amido-dienes in moderate to excellent yields (12 examples, up to 97%). The resulting chiral amido-dienes are employed as novel dienes in Diels-Alder (DA) reactions (58 examples, up to 93:7 dr, up to 70% yield). A range of chiral cyclic ketones were accessed upon hydrolysis, affording products with high levels of enantioselectivity (up to 92% ee, up to 81% yield).

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c00689

Authors: Aoibheann O’ Connor, Calvin Q. O’Broin, Julia Bruno-Colmenarez, Patrick J. Guiry

Institution: University College Dublin

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Science Foundation Ireland, Irish Research Council