Issue 7, 2023

Aromatization-driven cascade [1,5]-hydride transfer/cyclization for synthesis of spirochromanes

Abstract

An aromatization-driven hydride transfer-involved α-C(sp3)–H bond functionalization of the oxygen atom was developed. In this transformation, easily prepared p-quinone methides were applied as aromatic precursors to initiate a [1,5]-hydride transfer/cyclization reaction for generating cyclohexadienone fused spirochromanes. A variety of spirochromanes, including privileged molecules with two spirochromane moieties linked by an alkenyl or a phenyl group, were obtained in high efficiency. In addition, the derivatizations of products were conducted to further enrich the diversity of the structure.

Graphical abstract: Aromatization-driven cascade [1,5]-hydride transfer/cyclization for synthesis of spirochromanes

Supplementary files

Article information

Article type
Research Article
Submitted
10 Jan 2023
Accepted
28 Feb 2023
First published
08 Mar 2023

Org. Chem. Front., 2023,10, 1796-1802

Aromatization-driven cascade [1,5]-hydride transfer/cyclization for synthesis of spirochromanes

L. Cao, F. Hu, J. Dong, X. Zhang and S. Li, Org. Chem. Front., 2023, 10, 1796 DOI: 10.1039/D3QO00035D

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