Enantioselective Spirocyclization of Pd‐Enolates and Isocyanates

Abstract An enantioselective cyclization of Pd‐enolates and isocyanates to form spirocyclic γ‐lactams is reported. This reaction proceeds under mild reaction conditions and utilizes a novel Meldrum's acid derivative to achieve catalyst turnover, delivering enantioenriched products in up to 97% yield and 96% ee. Preliminary mechanistic investigations suggest that the reaction may proceed via the formation of higher‐order species.

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Publication Details

Journal
Angewandte Chemie
Published
2025-03-27
DOI
https://doi.org/10.1002/ange.202502583
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
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article

Enantioselective Spirocyclization of Pd‐Enolates and Isocyanates

Melinda Chan, Brian M. Stoltz, Kaylin N. Flesch, Jay P. Barbor et al.
Angewandte Chemie
Catalytic C–H Functionalization Methods
article

Enantioselective Spirocyclization of Pd‐Enolates and Isocyanates

Melinda Chan, Brian M. Stoltz, Kaylin N. Flesch, Jay P. Barbor, H Ang
article en

Abstract

Abstract An enantioselective cyclization of Pd‐enolates and isocyanates to form spirocyclic γ‐lactams is reported. This reaction proceeds under mild reaction conditions and utilizes a novel Meldrum's acid derivative to achieve catalyst turnover, delivering enantioenriched products in up to 97% yield and 96% ee. Preliminary mechanistic investigations suggest that the reaction may proceed via the formation of higher‐order species.

Angewandte ChemieVol. 137(23)
California Institute of Technology (US)
Openalex Percentile: Top 95%
Catalytic C–H Functionalization Methods
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