Use of a “Structural Dummy” α-Silyl Substituent in Nazarov Cyclization: Expanding the Substrate Scope to Indanones and Bicyclic 2-Pyrones

Organic Letters 2026

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Authors: Hyerim Kim, Jeongyeon Hwang, Gwanwoo Baek, J. E. Jung, Yonghoon Kwon
DOI: 10.1021/acs.orglett.5c04365
Cited by: 3
References: 86

Abstract

Aryl vinyl ketones, particularly those lacking an α-substituent, are among the most challenging substrates for Nazarov cyclization. We present a practical method to expand the scope of this reaction, enabling the efficient synthesis of indanones and bicyclic 2-pyrones. The use of an α-silyl substituent as a "structural dummy" enhances reactivity, and thus, the reaction proceeds under mild conditions. Notably, spontaneous desilylation during the reaction leaves the products with double-enolizable α-hydrogens, offering greater flexibility for functionalization at the α-position of the ketone.

Fields of Study & Subjects

Asymmetric Synthesis and Catalysis Catalytic Alkyne Reactions Catalytic Cross-Coupling Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
15
Pages
4649–4655
Publication date
5 January 2026
Language
EN