Synthesis of amino-cyclobutanes via [2+2] cycloadditions involving keteniminium intermediates

被引：39

作者：

Kolleth, Amandine ^{[1
]}

Lumbroso, Alexandre ^{[1
]}

Tanriver, Gamze ^{[2
]}

Catak, Saron ^{[2
]}

Sulzer-Mosse, Sarah ^{[1
]}

De Mesmaeker, Alain ^{[1
]}

机构：

[1] Syngenta Crop Protect AG, Crop Protect Res, Res Chem, Schaffhauserstr 101, CH-4332 Basel, Switzerland

[2] Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 25期

关键词：

Keteniminium salts; Cyclobutaniminiums; 2+2] cycloaddition; Aminocyclobutane; DFT calculations; STEREOSELECTIVE-SYNTHESIS; ELECTROPHILIC REARRANGEMENTS; CYCLOBUTENIMINIUM SALTS; DENSITY FUNCTIONALS; AMIDES; DERIVATIVES; PIPERIDINES; REACTIVITY; SOLUTES; ANALOGS;

D O I：

10.1016/j.tetlet.2016.04.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe an efficient method for the synthesis of aminocyclobutanes via a [2 + 2] cycloaddition between a keteniminium salt and an alkene, followed by a reduction step. The use of easily removable N-allyl moieties as protecting groups increases the potential of this method to access, in a few steps, highly functionalized cyclobutaneamine-containing building blocks. Moreover, DFT calculations verify the compatibility of N-allyl and N-propargyl keteniminiums in [2 + 2] cycloaddition reactions. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2697 / 2702

页数：6

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