Ring-Opening Cyclization (ROC) of Aziridines with Propargyl Alcohols: Synthesis of 3,4-Dihydro-2H-1,4-oxazines

被引：16

作者：

Singh, Bharat ^{[1
]}

Kumar, Manish ^{[1
]}

Goswami, Gaurav ^{[1
]}

Verma, Indresh ^{[1
]}

Ghorai, Manas K. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 07期

关键词：

ONE-POT SYNTHESIS; ACTIVATED AZIRIDINES; INTRAMOLECULAR HYDROAMINATION; ENANTIOSELECTIVE SYNTHESIS; 3+2 CYCLOADDITION; EPOXY-YNAMIDES; ACID; DERIVATIVES; EPOXIDES; N-SULFONYL-1,2,3-TRIAZOLES;

D O I：

10.1021/acs.joc.2c03093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Activated aziridines react with propargyl alcohols in the presence of Zn(OTf)2 as the Lewis acid catalyst following an SN2-type ring-opening mechanism to furnish the corresponding amino ether derivatives. Those amino ethers further undergo intramolecular hydroamination via 6-exo-dig cyclization in the presence of Zn(OTf)2 as the catalyst and tetrabutylammonium triflate salt as an additive under one-pot two-step reaction conditions. However, for nonracemic examples, ring opening and cyclization steps were conducted under two-pot conditions. The reaction works well without any additional solvents. The final 3,4-dihydro-2H-1,4-oxazine products were obtained with 13 to 84% yield and 78 to 98% enantiomeric excess (for nonracemic examples).

引用

页码：4504 / 4518

页数：15

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