Issue 59, 2019

Acid-catalyzed chirality-transferring intramolecular Friedel–Crafts cyclization of α-hydroxy-α-alkenylsilanes

Abstract

Acid-catalyzed intramolecular Friedel–Crafts cyclization of optically active α-hydroxy-α-alkenylsilanes possessing a benzene ring (>99% ee) with TMSOTf as a Lewis acid gave enantio-enriched tetrahydronaphthalenes (up to 98% ee). The silyl group attached to the chiral carbon played a crucial role in the chirality transfer.

Graphical abstract: Acid-catalyzed chirality-transferring intramolecular Friedel–Crafts cyclization of α-hydroxy-α-alkenylsilanes

Supplementary files

Article information

Article type
Communication
Submitted
07 May 2019
Accepted
01 Jul 2019
First published
09 Jul 2019

Chem. Commun., 2019,55, 8635-8638

Acid-catalyzed chirality-transferring intramolecular Friedel–Crafts cyclization of α-hydroxy-α-alkenylsilanes

K. Sakaguchi, S. Kubota, W. Akagi, N. Ikeda, M. Higashino, S. Ariyoshi, T. Shinada, Y. Ohfune and T. Nishimura, Chem. Commun., 2019, 55, 8635 DOI: 10.1039/C9CC03509E

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