Issue 22, 2018

Asymmetric vinylogous Mukaiyama aldol reaction of isatins under bifunctional organocatalysis: enantioselective synthesis of substituted 3-hydroxy-2-oxindoles

Abstract

A highly enantioselective organocatalytic vinylogous Mukaiyama aldol reaction of silyloxy dienes and isatins under bifunctional organocatalysis is presented. Substituted 3-hydroxy-2-oxindoles are synthesised in good yields and enantioselectivities. These synthetic intermediates are used for the construction of more complex molecules with biological properties such as the formal synthesis of a CB2 agonist presented.

Graphical abstract: Asymmetric vinylogous Mukaiyama aldol reaction of isatins under bifunctional organocatalysis: enantioselective synthesis of substituted 3-hydroxy-2-oxindoles

Supplementary files

Article information

Article type
Communication
Submitted
29 Jan 2018
Accepted
20 Feb 2018
First published
20 Feb 2018

Chem. Commun., 2018,54, 2781-2784

Asymmetric vinylogous Mukaiyama aldol reaction of isatins under bifunctional organocatalysis: enantioselective synthesis of substituted 3-hydroxy-2-oxindoles

V. Laina-Martín, J. Humbrías-Martín, J. A. Fernández-Salas and J. Alemán, Chem. Commun., 2018, 54, 2781 DOI: 10.1039/C8CC00759D

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