Intramolecular Imino-ene Reaction of 2H-azirines with Alkenes: Rapid Construction of Spiro NH Aziridines from Vinyl Azides

被引：15
作者：
Liu, Tai-Shang [1 ]
Zhou, Hao [1 ]
Chen, Peng [1 ]
Huang, Xiu-Rong [1 ]
Bao, Lin-Qing [1 ]
Zhuang, Chen-Lu [1 ]
Xu, Qing-Song [1 ]
Shen, Mei-Hua [1 ]
Xu, Hua-Dong [1 ]
机构：
[1] Changzhou Univ, Sch Pharmaceut Engn & Life Sci, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 11期
基金：
中国国家自然科学基金;
关键词：
DIELS-ALDER REACTIONS; NATURAL-PRODUCTS; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; OLEFINS; ACCESS; ALKYL; CYCLOADDITION; GENERATION; INHIBITORS;
D O I：
10.1021/acs.orglett.8b00821
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A range of novel (poly)cyclic alkaloids incorporating an unprecedented 1,S-diazaspiro[2.4]heptane core that carry a spiro NH aziridine moiety and a 7-vinyl group are constructed from the thermal reaction of vinyl azides with tethered alkenes. Vinyl azides are converted to 2H-azirines in situ, which serve as enophiles for intramolecular imino-ene reactions with suitable alkenes. High stereoselectivity and specificity have been achieved for this novel intramolecular imino-ene reaction of azirines.
引用
收藏
页码：3156 / 3160
页数：5
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