Enantioselective Spirocyclization of Pd‐Enolates and Isocyanates

J Jay P. Barbor (Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101–20 Pasadena CA 91125 USA) K Kaylin N. Flesch (Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101–20 Pasadena CA 91125 USA) M Melinda Chan (Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101–20 Pasadena CA 91125 USA) H Hannah R. Ang (Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101–20 Pasadena CA 91125 USA) B Brian M. Stoltz (The Warren and Katherine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, California 91125, United States)

Abstract

AbstractAn 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.

Article Details

Volume / Issue Vol. 64, Issue 23
Published June 02, 2025
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (5)

J

Jay P. Barbor

Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101–20 Pasadena CA 91125 USA

K

Kaylin N. Flesch

Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101–20 Pasadena CA 91125 USA

M

Melinda Chan

Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101–20 Pasadena CA 91125 USA

H

Hannah R. Ang

Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101–20 Pasadena CA 91125 USA

B

Brian M. Stoltz

The Warren and Katherine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, California 91125, United States