Synthesis of Chiral Spiro[4.5]decadienones via Chirality-Transferring Oxidative Intramolecular Cyclization of Allenylsilane-Tethered Phenols

Abstract

Reactions of phenols having a methylene-tethered chiral allenylsilane at the para position with a hypervalent iodine reagent result in chirality-transferring oxidative intramolecular cyclization accompanied by dearomatization of the phenol to stereoselectively give spiro[4.5]decadienones possessing a silylethynyl group.

Key words

allenylsilane - hypervalent iodine - chirality transfer - oxidative intramolecular cyclization - spirodienone - phenol

Publication History

Received: 14 March 2023

Accepted after revision: 17 April 2023

Accepted Manuscript online:
17 April 2023

Article published online:
05 June 2023

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