Diastereoselective Synthesis of 1,3-Oxazolidines via Cationic Iron Porphyrin-catalyzed Cycloaddition of Aziridines with Aldehydes

被引：23

作者：

Teranishi, Satoru ^{[1
]}

Maeda, Kazuki ^{[1
]}

Kurahashi, Takuya ^{[1
]}

Matsubara, Seijiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Mat Chem, Kyoto 6158510, Japan

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 08期

基金：

日本科学技术振兴机构;

关键词：

HIGH-VALENT METALLOPORPHYRIN; N-TOSYLAZIRIDINES; AZOMETHINE YLIDES; REARRANGEMENT; ALKYNES; CYCLOISOMERIZATION; CYCLOPROPANES; NITRILES; EPOXIDES; COMPLEX;

D O I：

10.1021/acs.orglett.9b00560

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient iron porphyrin Lewis acid-catalyzed cycloaddition of aziridines with aldehydes has been developed to provide oxazolidines with high regio- and diastereoselectivity. The cycloaddition proceeds in toluene with 1 mol % of the iron catalyst at 25 degrees C. A theoretical study and synchrotron-based X-rabsorption fine structure measurements provided fundamental insights into the aziridine iron porphyrin complex, which is the key intermediate for the generation of the 1,3-dipole synthon.

引用

页码：2593 / 2596

页数：4

共 35 条

[1] Cationic Iron(III) Porphyrin-Catalyzed [4+2] Cycloaddition of Unactivated Aldehydes with Simple Dienes
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[2] Synthesis of 1,3-oxazolidines from imines and epoxides catalyzed by samarium compounds
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[3] Construction of 1,3-Oxazolidines through a Three-Component [3+2] Cycloaddition of Tetrahydroisoquinolines, Aldehydes, and Ethyl Ketomalonate
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[4] Expedient iron-catalyzed stereospecific synthesis of triazines via cycloaddition of aziridines with diaziridines
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[6] Ytterbium(III) triflate catalyzed [3+2] cycloaddition of N-arylimines and epoxides:: A novel and solvent-free synthesis of substituted 1,3-oxazolidines
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[8] Silver-Catalyzed Diastereoselective Synthesis of Spirocyclic Pyrrolidine-Lactones by 1,3-Dipolar Cycloaddition
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[10] Ammonium Ferrate-Catalyzed Cycloaddition of CO2 to Aziridines for the Synthesis of 1,3-Oxazolidin-2-ones
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