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Issue 31, 2020
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BINOL derivatives-catalysed enantioselective allylboration of isatins: application to the synthesis of (R)-chimonamidine

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Abstract

The asymmetric synthesis of the 3-allyl-3-hydroxyoxindole skeleton was accomplished in yields up to 99% via a metal-free and enantioselective allylation of isatins (90–96% ee) using BINOL derivatives as catalysts and an optimized allylboronate. This methodology was applied at a gram-scale to the synthesis of the natural product (R)-chimonamidine.

Graphical abstract: BINOL derivatives-catalysed enantioselective allylboration of isatins: application to the synthesis of (R)-chimonamidine

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Article information


Submitted
06 Jul 2020
Accepted
24 Jul 2020
First published
28 Jul 2020

Org. Biomol. Chem., 2020,18, 6042-6046
Article type
Communication

BINOL derivatives-catalysed enantioselective allylboration of isatins: application to the synthesis of (R)-chimonamidine

J. Braire, V. Dorcet, J. Vidal, C. Lalli and F. Carreaux, Org. Biomol. Chem., 2020, 18, 6042
DOI: 10.1039/D0OB01386B

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