Work

Ring-Enlargement of in Situ Generated Cyclopropanones with Carbonyls and Imines: Synthesis of γ-Butyrolactones and -lactams

Year: 2026

Type: article

Abstract: We report a ring-enlargement of in situ generated cyclopropanones with aldehydes, ketones, and aldimines to access γ-butyrolactones and γ-lactams. Using bench-stable 1-sulfonylcyclopropanols as cyclopropanone precursors, the reaction proceeds under mild conditions and affords the products in yields of up to 84% across a range of carbonyl and imine coupling partners. Mechanistic experiments and DFT studies provide insight into the reaction pathway.

Source: Organic Letters

DOI: 10.1021/acs.orglett.6c00839

Authors: Marvin Lange, Arthur Semmelmaier, Richard Herzog, Heinrich F. von Köller, Daniel B. Werz

Institution: University of Freiburg

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Deutsche Forschungsgemeinschaft