Issue 15, 2023

Enantioselective Ni-catalyzed syn-hydrometalative cyclization of alkyne-tethered ketoamides to α-hydroxy-γ-lactams

Abstract

An enantioselective Ni-catalyzed syn-hydrocyclization of alkyne-tethered ketoamides for the synthesis of α-hydroxy γ-lactams is reported. Using Ni(OTs)2·6H2O/(S,S)-Me-Duphos as a precatalyst and (EtO)2MeSiH as a hydride source, a broad range of enantioenriched γ-lactams with a fully substituted stereogenic center are obtained in 32–84% yields with 87.5 : 12.5–97 : 3 er. Synthetic utilities, including scale-up reaction and product derivatization, are also demonstrated. This research presents a regioselective functionalization of alkynes and provides an efficient strategy to access functional group-enriched chiral heterocycles.

Graphical abstract: Enantioselective Ni-catalyzed syn-hydrometalative cyclization of alkyne-tethered ketoamides to α-hydroxy-γ-lactams

Supplementary files

Article information

Article type
Research Article
Submitted
08 May 2023
Accepted
16 Jun 2023
First published
20 Jun 2023

Org. Chem. Front., 2023,10, 3883-3888

Enantioselective Ni-catalyzed syn-hydrometalative cyclization of alkyne-tethered ketoamides to α-hydroxy-γ-lactams

H. Zeng, X. Zhang, Q. Li and W. Liu, Org. Chem. Front., 2023, 10, 3883 DOI: 10.1039/D3QO00670K

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