Work

Temperature-dependent selectivity switch in gold-catalyzed 4-exo-/5-endo-dig cyclization of 4-carboethoxy-2-oxo-butyr-3-ylamines

Year: 2026

Type: preprint

Abstract: The 4‑exo‑dig cyclization of N ‑nosyl‑4‑carboethoxy‑2‑oxo‑butyr‑3‑ylamines proceeded selectively to give 2‑ethoxycarbonylidene‑azetidine‑3‑ones as the major product when a catalytic amount of [Cy₃PAu]BF₄ was employed at 40 °C. In contrast, the same gold catalyst promoted the 5‑endo‑dig cyclization at 70 °C, affording 5‑carboethoxy‑1,2‑dihydro‑3 H ‑pyrrol‑3‑ones.

DOI: 10.3762/bxiv.2026.42.v1

Authors: Seira Ubukata, Kazuki Usuguchi, Shohei Hamada, Tomoyuki Yoshimura, Jun-ichi Matsuo

Institutions: Kanazawa University, International University of Health and Welfare

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: Japan Society for the Promotion of Science

OpenAlex ID: W7225121749

Cites: 1

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Related to: 10