Organocatalytic synthesis of densely functionalized oxa-bridged 2,6epoxybenzo[ b][1,5] oxazocine heterocycles

被引：17

作者：

Gurubrahamam, Ramani ^{[1
]}

Nagaraju, Koppanathi ^{[1
]}

Chen, Kwunmin ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, 88 Sec 4,Tingchow Rd, Taipei 11677, Taiwan

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 47期

关键词：

ONE-POT ACCESS; CHIRAL IMINOPHOSPHORANE CATALYSIS; HIGHLY ENANTIOSELECTIVE SYNTHESIS; INTRAMOLECULAR 4+2 CYCLOADDITION; ELECTRON-DEFICIENT ALKYNES; ORTHO-QUINONE METHIDES; PI-CATION CATALYSTS; ASYMMETRIC-SYNTHESIS; BRONSTED ACID; 1,3-DIPOLAR CYCLOADDITION;

D O I：

10.1039/c8cc02565g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Metal-free addition of salicylhydrazones to electron deficient internal alkynes catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield oxa-bridged 2,6-epoxybenzo[b][1,5]oxazocine heterocycles was achieved. The demonstrated protocol proceeds through an o-quinone methide formation, aza-Michael addition, stereoselective protonation, enamine promoted aromatization, O,O-acetalization and O,N-aminalization sequence to provide privileged heterocycles in good yields with high diastereoselectivities.

引用

页码：6048 / 6051

页数：4

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