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

被引：13

作者：

Han, Xiaoli ^{[1
,2
]}

Nie, Xiaodi ^{[1
,2
]}

Feng, Yiman ^{[1
,2
]}

Wei, Bangguo ^{[1
,2
]}

Si, Changmei ^{[1
,2
]}

Lin, Guoqiang ^{[3
]}

机构：

[1] Fudan Univ, Inst Biomed Sci, Shanghai 200433, Peoples R China

[2] Fudan Univ, Sch Pharm, Shanghai 200433, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2021年 / 32卷 / 11期

基金：

中国国家自然科学基金;

关键词：

N-acyliminium ions; Simple olefins; Intermolecular [4+2] process; Substituted-1,3-oxazinan-2-ones; Spiro; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALKOXYCARBONYLIMINIUM IONS; STEREOCONTROLLED SYNTHESIS; ADDITION-REACTIONS; CONCISE SYNTHESIS; ALKALOIDS; CARBON; HETEROCYCLES; ALCOHOLS;

D O I：

10.1016/j.cclet.2021.05.003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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 1,1disubstituted 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. (C) 2021 Published by Elsevier B.V. onbehalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

引用

页码：3526 / 3530

页数：5

共 7 条

[1] Aza-[4+2] cycloadditions employing catalytically derived N-acyliminium ions
Owen, Niamh J.
McLaughlin, Mark G.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (42) : 8209 - 8211
[2] A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
Lu, Nianhong
Wang, Lihong
Li, Zhanshan
Zhang, Wei
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 192 - 200
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[4] Stereoselective Intermolecular [4+2] Process of N,O-acetals with Terminal Alkynes for Construction of Functional cis-Pyrido and Pyrrolo[1,2-c][1,3]oxazin-1-ones
Wang, Chen
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ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (04) : 822 - 831
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Si, Chang-Mei
Wei, Bang-Guo
TETRAHEDRON LETTERS, 2021, 67
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Jiang, Yang-Jie
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Ding, Chang-Hua
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ORGANIC LETTERS, 2020, 22 (14) : 5375 - 5379

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