Citation: Xiaoli Han, Xiaodi Nie, Yiman Feng, Bangguo Wei, Changmei Si, Guoqiang Lin. Intermolecular [4 + 2] process of N-acyliminium ions with simple olefins for construction of functional substituted-1, 3-oxazinan-2-ones[J]. Chinese Chemical Letters, ;2021, 32(11): 3526-3530. doi: 10.1016/j.cclet.2021.05.003 shu

Intermolecular [4 + 2] process of N-acyliminium ions with simple olefins for construction of functional substituted-1, 3-oxazinan-2-ones

Xiaoli Han ^a ,
Xiaodi Nie ^a ,
Yiman Feng ^a ,
Bangguo Wei ^{a, *,} ,
Changmei Si ^{a, *,} ,
Guoqiang Lin ^b

a.
Institutes of Biomedical Sciences and School of Pharmacy, Fudan University, Shanghai 200433, China
b.
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

bgwei1974@fudan.edu.cn

sicm@fudan.edu.cn

Received Date: 18 March 2021
Revised Date: 1 May 2021
Accepted Date: 6 May 2021
Available Online: 15 May 2021

Figures(7)

An efficient approach to functionalized 4, 6-disubstituted-and 4, 6, 6-trisubstituted-1, 3-oxazinan-2-ones skeleton has been developed through the reaction of semicyclic N, O-acetals 4a and 4b with 1, 1- disubstituted ethylenes 5 or 8. As a result of such a [4 + 2] cycloaddition process, 4, 6, 6-trisubstituted- 1, 3-oxazinan-2-ones 6aa, 6af-6au, 7ba, 7bf-7bw and 6, 6-spiro containing 1, 3-oxazinan-2-ones 9ad, 9ae, 10ba-10bg were obtained in 36%-96% yields and with moderate to excellent diastereoselectivities. In addition, the synthesis of (±)-norallosedamine 12 could be conveniently achieved from the cycloadduct 7bf.
- N-acyliminium ions,
- Simple olefins,
- Intermolecular [4 + 2] process,
- Substituted-1, 3-oxazinan-2-ones,
- Spiro
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