Improved synthesis of 8-oxabicyclo[3.2.1]octanes via tandem C-H oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization

Lin Liu; Hai-Long Cheng; Wen-Qiang Ma; Si-Hua Hou; Yong-Qiang Tu; Fu-Min Zhang; Xiao-Ming Zhang; Shao-Hua Wang

doi:10.1039/c7cc08511g

Improved synthesis of 8-oxabicyclo[3.2.1]octanes via tandem C-H oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization

Chem Commun (Camb). 2018 Jan 7;54(2):196-199. doi: 10.1039/c7cc08511g. Epub 2017 Dec 11.

Authors

Lin Liu¹, Hai-Long Cheng¹, Wen-Qiang Ma¹, Si-Hua Hou¹, Yong-Qiang Tu², Fu-Min Zhang¹, Xiao-Ming Zhang¹, Shao-Hua Wang¹

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry & School of Pharmacy, Lanzhou University, Lanzhou 730000, P. R. China. tuyq@lzu.edu.cn wangshh@lzu.edu.cn.
² State Key Laboratory of Applied Organic Chemistry & School of Pharmacy, Lanzhou University, Lanzhou 730000, P. R. China. tuyq@lzu.edu.cn wangshh@lzu.edu.cn and School of Chemistry & Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China. tuyq@sjtu.edu.cn.

PMID: 29226934
DOI: 10.1039/c7cc08511g

Abstract

A tandem C-H oxidation/oxa-[3,3] Cope rearrangement/aldol reaction of allylic silylethers promoted by T⁺BF₄^-(tempo oxoammonium tetrafluoroborate)/ZnBr₂ has been successfully developed allowing the efficient construction of 8-oxabicyclo[3.2.1]octanes and their analogs with a wide substrate scope.