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March 3, 2026Organic Letters0 citations

Palladium-Catalyzed Enantioselective Dearomatization of Furan To Access N , O -Spirocycles

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XWXinyue WangCMChun MaJYJunfeng Yang

Key Points

  • Enantioselective dearomatization yielded spirocycles with high selectivity and excellent Z/E ratio, showcasing its efficacy.
  • The method utilized a newly developed chiral sulfinamide phosphine ligand, enhancing the reaction's efficiency.
  • Mild reaction conditions were successfully implemented, making this protocol more accessible for various applications.
  • This study highlights the synthetic versatility of N,O-spirocycles in the development of pharmaceuticals and chiral ligands.

Abstract

N,O-Spirocycles are important structural motifs in efficient chiral ligands, natural products, and pharmaceuticals. However, the achievement of highly enantioselective N,O-spirocycles remains a challenge. Herein, we present a Pd-catalyzed enantioselective dearomatization of bromofurans with N-tosylhydrazones using a newly developed chiral sulfinamide phosphine ligand. The reaction features an excellent Z/E ratio, high enantioselectivity, and mild reaction conditions. The synthetic versatility of N,O-spirocycles is demonstrated.

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Cite This Study

Wang et al. (2026) studied this question.

synapsesocial.com/papers/69a75cc5c6e9836116a25ebehttps://doi.org/10.1021/acs.orglett.5c05263
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