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

Organic Letters 2026 Open access

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Authors: Marvin Lange, Arthur Semmelmaier, Richard Herzog, Heinrich F. von Köller, Daniel B. Werz
DOI: 10.1021/acs.orglett.6c00839
Cited by: 1
References: 63

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.

Fields of Study & Subjects

Cyclopropane Reaction Mechanisms Catalytic C–H Functionalization Methods Organic and Inorganic Chemical Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
15
Pages
4783–4788
Publication date
1 April 2026
Language
EN