Catalytic Enantioselective Synthesis of 1,4-Benzodioxepines

Xi Zou, Guangwu Sun, Hai Huang, Jinping Wang*, Wen Yang* and Jianwei Sun*

*Hunan University, Changsha 410082; The Hong Kong University of Science and Technology, Hong Kong SAR, P.R. China, Email: jinpingwang1985126.com, yangwenhnu.edu.cn, sunjwust.hk

X. Zou, G. Sun, H. Huang, J. Wang, W. Yang, J. Sun, Org. Lett., 2020, 22, 249-252.

DOI: 10.1021/acs.orglett.9b04244

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Abstract

A chiral phosphoric acid catalyzes an intramolecular reaction of a range of benzylic alcohols bearing an internal oxetane to form chiral 1,4-benzodioxepines with high enantioselectivity. This oxetane desymmetrization process enables a direct synthesis of seven-membered heterocycles with good stereocontrol.

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Key Words

benzo-fused O-hetercycles, organocatalysis

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ID: J54-Y2020