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

页码：3156 / 3160

页数：5

共 3 条

[1] BORON-TRIFLUORIDE CATALYZED REACTION OF 2H-AZIRINES AND VINYL AZIDES WITH NITRILES
BADER, H
HANSEN, HJ
CHIMIA, 1975, 29 (06) : 264 - 266
[2] A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach
Andresini, Michael
Degennaro, Leonardo
Luisi, Renzo
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 203 - 209
[3] Transition Metal-Catalyzed Synthesis of 3-Coumaranone-Containing NH-Aziridines from 2H-Azirines: Nickel(II) versus Gold(I)
Sakharov, Pavel A.
Rostovskii, Nikolai V.
Khlebnikov, Alexander F.
Khoroshilova, Olesya V.
Novikov, Mikhail S.
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (14) : 3359 - 3372

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