Work

Cooperative Rh 2 (OAc) 4 /Chiral Phosphoric Acid‐Catalyzed (3 + 3)‐Cycloadditions of Pyrrole‐3‐Methides and Carbonyl Ylides

Year: 2025

Type: article

Abstract: A stereoselective (3 + 3)‐cycloaddition between pyrrole‐3‐methides and carbonyl ylides, both generated in situ, has been developed to access densely substituted oxa‐bridged cyclohepta[1,2‐ b ]pyrroles in a single synthetic step. This transformation is enabled by a cooperative dual‐catalytic system comprising rhodium(II) acetate and a chiral phosphoric acid, each operating in separate catalytic cycles to generate the key transient intermediates. The reaction delivers structurally complex products bearing three stereogenic centers, two of which are quaternary. Excellent yields, high levels of enantioselectivity, and low to moderate diastereoselectivity are additional key features of this process. This methodology provides a straightforward synthetic access to valuable heterocyclic scaffolds with potential applications in synthetic and medicinal chemistry.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.70180

Authors: Philipp Stehr, Christoph Schneider

Institution: Leipzig University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,650

Funder: Deutsche Forschungsgemeinschaft