期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 15, 页码 7907-7918出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00788
关键词
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资金
- IIT-Kanpur
- CSIR, India
- UGC, India
Novel 3,4-dihydro-1,4-benzoxazine derivatives have been synthesized by an efficient and simple method in excellent enantio- and diastereospecificity (ee > 99%, de > 99%). The reaction proceeds via Lewis acid -catalyzed S(N)2-type ring opening of activated aziridines with 2-halophenols followed by Cu(I)-catalyzed intramolecular C-N cyclization in a stepwise fashion under one-pot conditions to furnish the 3,4-dihydro-1,4-benzoxazine derivatives in excellent yields (up to 95%). The strategy offers a short and efficient synthesis to (S)-3-methyl-1,4-benzoxazine (S) -3v, a late stage intermediate in the synthesis of levofloxacin.
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