Work

Asymmetric [3 + 2] Cycloaddition to Access 3‐Pyrrolines and Their Switchable Transformations to Nine‐Membered Cyclic Sulfamidates and 2 H ‐Pyrroles

Year: 2025

Type: article

Abstract: Herein, Pd-catalyzed asymmetric [3 + 2] cycloaddition and olefin isomerization is reported to afford chiral 3-pyrrolines using cyano-TMM (trimethylenemethane) and cyclic sulfamidate imines. This represents a unique protocol to provide chiral N-heterocycles bearing endocyclic olefins by asymmetric Pd-TMM cycloaddition. The developed Pd-catalyzed cycloaddition further extends to versatile synthetic transformations, offering a facile and unified approach to synthetically challenging yet valuable classes of heterocycles, including medium-sized sulfamidate rings and 2H-pyrroles, in a one-pot operation. In particular, chemo-switchable ring expansion and desulfonylation of sulfamidate-fused 3-pyrrolines are achieved by simple solvent and temperature changes under identical alkoxide base conditions.

Source: Advanced Science

DOI: 10.1002/advs.202513904

Authors: Seoung‐Mi Choi, Jong‐Un Park, Ju Hyun Kim

Institutions: Dongguk University, Gyeongsang National University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $6,730

Funders: National Research Foundation, National Research Foundation of Korea