Expeditious access to cis-β-aryl, γ-alkyl disubstituted (±)-γ-butyrolactones via nickel-hydride catalysis

Ojo, O. S. , Steel, H. J. and Miras, H. N. (2023) Expeditious access to cis-β-aryl, γ-alkyl disubstituted (±)-γ-butyrolactones via nickel-hydride catalysis. Organic and Biomolecular Chemistry, 21(33), pp. 6738-6742. (doi: 10.1039/D3OB00895A) (PMID:37551644)

Abstract

The 1,4-reduction of β- and γ-substituted butenolides using 5 mol% of NiCl₂·6H₂O and NaBH₄ in MeOH for rapid access to cis-β,γ-disubstituted γ-butyrolactones is described. The reaction was selective for cis-products, which were obtained in good to excellent yields. This study showcased the influence of steric hindrance and angle strain on the diastereoselectivity outcome of conjugate reductions facilitated by in situ generated nickel-hydride.

• Item Type: Articles
• Additional Information: Financial support from the School of Chemistry, University of Glasgow is gratefully acknowledged.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Moiras, Professor Haralampos and Ojo, Dr Oluwarotimi
• Authors: Ojo, O. S., Steel, H. J., and Miras, H. N.
• 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: 01 August 2023
• Copyright Holders: Copyright © 2023 The Royal Society of Chemistry
• First Published: First published in Organic and Biomolecular Chemistry 21(33):6738-6742
• Publisher Policy: Reproduced under a Creative Commons License