Formation of substituted 2-iminooxazolidines via intermolecular 1,2-addition/intramolecular N-vinylation using 3-substituted-2-bromo-2-propen-1-ols as substrates

被引：4

作者：

Weischedel, Heike ^{[1
]}

Schmidt, Dietmar ^{[1
]}

Conrad, Juergen ^{[1
]}

Beifuss, Uwe ^{[1
]}

机构：

[1] Univ Hohenheim, Inst Chem, Bioorgan Chem, Garbenstr 30, D-70599 Stuttgart, Germany

来源：

TETRAHEDRON | 2018年 / 74卷 / 44期

关键词：

1,2-Addition; N-Vinylation; Copper; Cross-coupling; Domino reaction; DOMINO ADDITION/DOUBLE CYCLIZATION; COPPER-CATALYZED SYNTHESIS; ONE-STEP SYNTHESIS; BENZIMIDAZOLE DERIVATIVES; PROPARGYLIC ALCOHOLS; REACTIONS EFFICIENT; SELECTIVE SYNTHESIS; PEPTIDE-SYNTHESIS; BUILDING-BLOCKS; O-HALOANILINES;

D O I：

10.1016/j.tet.2018.08.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Cu2O-catalyzed reaction between equimolar amounts of easily available 3-substituted-2-bromo-2-propen-1-ols and dicyclohexyl carbodiimide in DMSO at 100 degrees C using K3PO4 as the base and in the absence of any additive exclusively delivers substituted 2-iminooxazolidines with yields up to 80%. The highly selective transformation is assumed to start with an intermolecular 1,2-addition, which is followed by an intramolecular N-vinylation. The products can also be obtained in the absence of Cu2O, albeit in lower yields. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：6426 / 6441

页数：16

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