Issue 33, 2023
From the journal:

Organic & Biomolecular Chemistry

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

O. Stephen Ojo, ORCID logo *a   Hannah J. Steela  and  Haralampos N. Miras ORCID logo a  

* Corresponding authors

a WestCHEM, School of Chemistry, University of Glasgow, The Joseph Black Building, Glasgow, UK
E-mail: Oluwarotimi.ojo@glasgow.ac.uk

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.

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

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Article information

DOI
https://doi.org/10.1039/D3OB00895A
Article type
Paper
Submitted
05 Jun 2023
Accepted
31 Jul 2023
First published
01 Aug 2023
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2023,21, 6738-6742

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

O. S. Ojo, H. J. Steel and H. N. Miras, Org. Biomol. Chem., 2023, 21, 6738 DOI: 10.1039/D3OB00895A

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