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

作　　者：Xiaoli Han Xiaodi Nie Yiman Feng Bangguo Wei Changmei Si Guoqiang Lin 

机构地区：[1]Institutes of Biomedical Sciences and School of Pharmacy,Fudan University,Shanghai 200433,China [2]Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China

出　　处：《Chinese Chemical Letters》2021年第11期3526-3530,共5页中国化学快报（英文版）

基　　金：the National Natural Science Foundation of China(No.21772027 to B.-G.Wei and 21702032 to C.-M.Si)for financial support.

摘　　要：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.

关 键 词：N-acyliminium ions Simple olefins Intermolecular[4+2]process Substituted-1 3-oxazinan-2-ones Spiro 

分 类 号：O621.25[理学—有机化学]