Tetrahedron p. 7115 - 7128 (1999)
Update date:2022-07-30
Topics:
Liu, Ju-Tsung
Lin, Wen-Wei
Jang, Jeong-Jiunn
Liu, Jing-Yuan
Yan, Ming-Chung
Hung, Chihua
Kao, Kuo-Hsi
Wang, Yeh
Yao, Ching-Fa
The Michael addition reactions of β-nitrostyrenes 1 with 4-pentene-1- magnesium bromide 2a or 3-butene-1-magnesium bromide 2b generated nitronates 3 or 4. Medium to high yields of isoxazolidine derivatives 9 and 10 were obtained when nitronates 3 or 4 were treated with ethyl chloroformate and catalytic amount of 4-dimethylaminopyridine (DMAP) at room temperature in one-pot and the ratios of trans-9:cis-9 were from 1:3.00 to 1:4.06 and the ratios of trans-10:cis-1 0 were >99:1. The formation of compounds 9 is proposed to proceed through intramolecular nitrile oxide-olefin cycloadditions (INOC) because compounds 14a-d, obtained from the trapping of the nitrile oxides by ethyl chloroformate, could be isolated. The mechanism of the generation of compounds 10 is proposed to proceed through intramolecular alkoxycarbonyl nitronate-olefin cycloadditions (IAOC) to form intermediates N-(ethoxycarbonyl)isoxazolidines 13 and then eliminate EtOH and CO2 (or EtOCO2H) to yield the final products.
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Doi:10.1002/ejoc.201900648
(2019)Doi:10.1016/S0040-4020(99)00378-6
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(2021)Doi:10.1016/S0031-9422(82)85059-0
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(1988)Doi:10.1016/S0960-894X(99)00248-6
(1999)