Synthesis of Nonracemic 1,4-Benzoxazines via Ring Opening/Cyclization of Activated Aziridines with 2-Halophenols: Formal Synthesis of Levofloxacin

Abhijit Mal, Imtiyaz Ahmad Wani, Gaurav Goswami and Manas K. Ghorai*

*Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India, Email: mkghoraiiitk.ac.in

A. Mal, I. A. Wani, G. Goswami, M. K. Ghorai, J. Org. Chem., 2018, 83, 7907-7918.

DOI: 10.1021/acs.joc.8b00788

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Abstract

An efficient synthesis of 3,4-dihydro-1,4-benzoxazine derivatives in excellent enantio- and diastereospecificity (ee > 99%, de > 99%) proceeds via Lewis acid-catalyzed S_N2-type ring opening of activated aziridines with 2-halophenols followed by Cu(I)-catalyzed intramolecular C-N cyclization in a stepwise fashion.

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Key Words

3,4-Dihydro-2H-1,4-benzoxazines

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ID: J42-Y2018