Acid-catalyzed chirality-transferring intramolecular Friedel–Crafts cyclization of α-hydroxy-α-alkenylsilanes. Issue 59 (9th July 2019)

• Record Type: Journal Article
• Authors: Sakaguchi, Kazuhiko; Kubota, Shunnichi; Akagi, Wataru; Ikeda, Naoko; Higashino, Masato; Ariyoshi, Shoma; Shinada, Tetsuro; Ohfune, Yasufumi; Nishimura, Takahiro
• Is Part Of: Chemical communications. Volume 55:Issue 59(2019)
• Page Start: 8635
• Page End: 8638
• Publication Date: 2019-07-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc03509e
• Languages: English
• ISSNs: 1359-7345

Abstract

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). 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.