An expedient copper-catalysed asymmetric synthesis of γ-lactones and γ-lactams. Application to the synthesis of lucidulactone A

Ojo, O. S. , Hughes, D. L. and Richards, C. J. (2023) An expedient copper-catalysed asymmetric synthesis of γ-lactones and γ-lactams. Application to the synthesis of lucidulactone A. Organic and Biomolecular Chemistry, 21(19), pp. 4144-4149. (doi: 10.1039/D3OB00563A) (PMID:37132994)

Abstract

The parent Josiphos ligand gave excellent ee values (95–99%) and good yields (60–97%) in the copper-catalysed asymmetric conjugate reduction of β-aryl α,β-unsaturated lactones and lactams with PMHS. The substrates were obtained from stereospecific copper-catalysed addition of arylboronic acids to alkynoates followed by deprotection and cyclisation. The acyclic lactam precursors also underwent reduction with good ee values (83–85%) and yields (79–95%). Application of this asymmetric reduction methodology included the synthesis of natural product lucidulactone A.

• Item Type: Articles
• Additional Information: The Leverhulme Trust (RPG-2018-270) (O. S. O.) is thanked for financial support.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Ojo, Dr Oluwarotimi
• Authors: Ojo, O. S., Hughes, D. L., and Richards, C. J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic and Biomolecular Chemistry
• Publisher: Royal Society of Chemistry
• ISSN: 1477-0520
• ISSN (Online): 1477-0539
• Published Online: 24 April 2023
• Copyright Holders: Copyright © 2023 The Royal Society of Chemistry
• First Published: First published in Organic and Biomolecular Chemistry 21(19):4144-4149
• Publisher Policy: Reproduced under a Creative Commons License