3 years ago

Enantioselective Synthesis of Functionalized β-Lactones by NHC-Catalyzed Aldol Lactonization of Ketoacids

Enantioselective Synthesis of Functionalized β-Lactones by NHC-Catalyzed Aldol Lactonization of Ketoacids
Santigopal Mondal, Tamal Kanti Das, Akkattu T. Biju, Rajesh G. Gonnade, Subrata Mukherjee
N-Heterocyclic carbene (NHC)-catalyzed intramolecular aldol lactonization of readily available ketoacids leading to the enantioselective synthesis of cyclopentane-fused β-lactones is presented. The reaction proceeds via the generation of NHC-bound enolate intermediates formed from the ketoacids in the presence of the peptide coupling reagent HATU and NHC generated from the chiral triazolium salt. The functionalized β-lactones are formed under mild conditions in high yields and enantioselectivities.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01526

DOI: 10.1021/acs.joc.7b01526

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