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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening †

by
Alastair J. Nimmo
,
Kevin Kasten
,
George White
,
Julia Roeterdink
,
Aidan P. McKay
,
David B. Cordes
and
Andrew David Smith
*
EaStCHEM, School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
*
Author to whom correspondence should be addressed.
†
Dedication: This manuscript is dedicated to the long-standing achievements of Prof. John Walton (University of St Andrews) and his dedication to understanding synthetic chemistry.
Molecules 2024, 29(15), 3635; https://doi.org/10.3390/molecules29153635 (registering DOI)
Submission received: 28 June 2024 / Revised: 29 July 2024 / Accepted: 29 July 2024 / Published: 31 July 2024
(This article belongs to the Special Issue Radicals, Mechanisms and Synthesis: A Themed Issue in Honor of the Many Contributions of Prof. Dr. John C. Walton)
Review Reports Versions Notes

Abstract

Malamides (diamide derivatives of malic acid) are prevalent in nature and of significant biological interest, yet only limited synthetic methods to access functionalised enantiopure derivatives have been established to date. Herein, an effective synthetic method to generate this molecular class is developed through in situ formation of spirocyclic β-lactone-oxindoles (employing a known enantioselective isothiourea-catalysed formal [2+2] cycloaddition of C(1)-ammonium enolates and isatin derivatives) followed by a subsequent dual ring-opening protocol (of the β‑lactone and oxindole) with amine nucleophiles. The application of this protocol is demonstrated across twelve examples to give densely functionalised malamide derivatives with high enantio- and diastereo-selectivity (up to >95:5 dr and >99:1 er).
Keywords: malamides; organocatalysis; isothiourea; β-lactone ring-opening; oxindole ring-opening; asymmetric synthesis; [2+2] cycloaddition malamides; organocatalysis; isothiourea; β-lactone ring-opening; oxindole ring-opening; asymmetric synthesis; [2+2] cycloaddition

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MDPI and ACS Style

Nimmo, A.J.; Kasten, K.; White, G.; Roeterdink, J.; McKay, A.P.; Cordes, D.B.; Smith, A.D. One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening. Molecules 2024, 29, 3635. https://doi.org/10.3390/molecules29153635

AMA Style

Nimmo AJ, Kasten K, White G, Roeterdink J, McKay AP, Cordes DB, Smith AD. One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening. Molecules. 2024; 29(15):3635. https://doi.org/10.3390/molecules29153635

Chicago/Turabian Style

Nimmo, Alastair J., Kevin Kasten, George White, Julia Roeterdink, Aidan P. McKay, David B. Cordes, and Andrew David Smith. 2024. "One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening" Molecules 29, no. 15: 3635. https://doi.org/10.3390/molecules29153635

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