Use of allylzinc halide as a source of halide: Differential addition of nucleophiles to Ts-aziridines and aldehydes under similar reaction conditions

被引：11

作者：

Chatterjee, Rana ^{[1
]}

Samanta, Satyajit ^{[1
]}

Mukherjee, Anindita ^{[2
]}

Santra, Sougata ^{[2
]}

Zyryanov, Grigory V. ^{[2
,3
]}

Majee, Adinath ^{[1
]}

机构：

[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India

[2] Ural Fed Univ, Chem Engn Inst, Dept Organ & Biomol Chem, 19 Mira St, Ekaterinburg 620002, Russia

[3] Russian Acad Sci, Ural Div, I Ya Postovskiy Inst Organ Synth, 22 S Kovalevskoy St, Ekaterinburg 620219, Russia

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 03期

基金：

俄罗斯科学基金会;

关键词：

Aziridine; Allylic halides; Halogenations; Carbonyls; Allylation; BOND-FORMING REACTIONS; HOMOALLYLIC ALCOHOLS; PROMOTED ALLYLATION; N-TOSYLAZIRIDINES; CARBONYL ADDITION; IONIC LIQUID; RING; INDIUM; SALT; EPOXIDES;

D O I：

10.1016/j.tetlet.2018.12.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have observed that the allylic zinc halide under identical reaction conditions acts in different modes for different electrophiles. For Ts-aziridines the halide part of the allylic halide has been introduced as a nucleophile and for the carbonyl compounds the simple allylation reaction occurs. To the best of our knowledge this is the first report where the allylic zinc halide is the source of halide acting as nucleophile. The main advantages of the present procedure are easy to handle, no need of inert atmosphere, mild reaction conditions, and applicability to a wide variety of substrates for aziridines and carbonyl compounds. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：276 / 283

页数：8

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