Lewis-Acid-Catalyzed Cyclization of Bicyclo[1.1.0]butanes with Alkenyl Cyclic Dithioacetals for the Synthesis of 11-Membered Bicyclic Medium-Sized Rings

Organic Letters 2026

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Authors: H Chen, Junmin Zhang, Lihang Cao, H Chen, Hui Guo, Yi Hua, Xiaoze Bao, Zhikun Yang, H Wang
DOI: 10.1021/acs.orglett.6c01548
Cited by: 1
References: 61

Abstract

Medium-sized rings are valuable synthetic scaffolds yet challenging to construct. Herein, we report a Lewis-acid-catalyzed (8 + 3) cycloaddition of bicyclo[1.1.0]butanes with alkenyl cyclic dithioacetals that provides efficient access to previously inaccessible 11-membered bicyclo[8.1.1] skeletons. Driven by strain release and catalyzed by Lu(OTf) 3, this ring expansion proceeds under mild conditions, exhibits a broad substrate scope, and delivers products in excellent yields (46 examples, with yields up to 94%). Mechanistic studies and DFT calculations support a pathway involving sequential nucleophilic attack, ring opening, and regioselective intramolecular 1,4-addition.

Fields of Study & Subjects

Radical Photochemical Reactions Synthetic Organic Chemistry Methods Synthesis of heterocyclic compounds

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
23
Pages
7158–7163
Publication date
2 June 2026
Language
EN