Synthesis of 6- oxa-Spiro[4.5]decane Derivatives by Merging Ring-Opening of Benzo[ c]oxepines and Formal 1,2-Oxygen Migration

Yong-Dong Du; Lin-Lin Ma; Chun-Yan Wu; Rong-He Wu; Zhi-Cheng Yu; You Zhou; Dong-Sheng Yang; Yan-Dong Wu; Jun-Gang Wang; An-Xin Wu

doi:10.1021/acs.joc.4c02206

Synthesis of 6- oxa-Spiro[4.5]decane Derivatives by Merging Ring-Opening of Benzo[ c]oxepines and Formal 1,2-Oxygen Migration

J Org Chem. 2024 Nov 1;89(21):15953-15963. doi: 10.1021/acs.joc.4c02206. Epub 2024 Oct 16.

Authors

Yong-Dong Du¹, Lin-Lin Ma¹, Chun-Yan Wu², Rong-He Wu¹, Zhi-Cheng Yu², You Zhou², Dong-Sheng Yang², Yan-Dong Wu², Jun-Gang Wang¹, An-Xin Wu^{2

3}

Affiliations

¹ School of Chemical Engineering, Guizhou Minzu University, Guizhou, Guiyang 550025, P. R. China.
² State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.
³ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.

PMID: 39413407
DOI: 10.1021/acs.joc.4c02206

Abstract

A facile one-pot synthetic method has been developed for constructing 6-oxa-spiro[4.5]decane skeletons by merging the ring-opening of benzo[c]oxepines and formal 1,2-oxygen migration reactions. More than 30 examples of the 6-oxa-spiro[4.5]decane derivatives have been synthesized under transition-metal-free conditions.