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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Xinyue Wang
Chun Ma
Junfeng Yang
Organic Letters
Fudan University
Yangzhou University
Henan Normal University
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Wang et al. (Wed,) studied this question.
www.synapsesocial.com/papers/69a75cc5c6e9836116a25ebe — DOI: https://doi.org/10.1021/acs.orglett.5c05263