Domino Michael/aza-Wittig reaction in the diastereoselective construction of spiro[azepane-4,3′-oxindoles]

被引：8
作者：
Ivanov, Konstantin L. [1 ]
Kravtsova, Anna A. [1 ]
Kirillova, Elena A. [1 ]
Melnikov, Mikhail Ya [1 ]
Budynina, Ekaterina M. [1 ]
机构：
[1] Lomonosov Moscow State Univ, Dept Chem, Leninskie Gory 1-3, Moscow 119991, Russia
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 30期
基金：
俄罗斯科学基金会;
关键词：
Spirooxindole; Azepane Michael addition; aza-Wittig reaction; ASYMMETRIC-SYNTHESIS; DERIVATIVES; SPIROOXINDOLES;
D O I：
10.1016/j.tetlet.2019.06.037
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient synthetic strategy for the diastereoselective assembly of spiro[azepane-4,3'-oxindoles] was developed via a Staudinger/Michael/aza-Wittig/reduction/N-deprotection reaction sequence starting from PMB-protected oxindole-substituted ethylazides. The key step of the method is a domino self-catalytic Michael/aza-Wittig reaction wherein the phosphazene moiety acts first as the catalyst and then as the reactant, resulting in the formation of a seven-membered N-heterocycle. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1952 / 1955
页数：4
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