Vinylphosphonium Salt-Mediated Reactions: A One-Pot Condensation Approach for the Highly cis-Selective Synthesis of N-Benzoylaziridines and the Green Synthesis of 1,4,2-Dioxazoles as Two Important Classes of Heterocyclic Compounds

被引：57

作者：

Aghahosseini, Hamideh ^{[1
]}

Ramazani, Ali ^{[1
]}

Jalayer, Nastaran Safarvand ^{[1
]}

Ranjdoost, Zahra ^{[1
]}

Souldozi, Ali ^{[2
]}

Slepokura, Katarzyna ^{[3
]}

Lis, Tadeusz ^{[3
]}

机构：

[1] Univ Zanjan, Dept Chem, POB 45195-313, Zanjan, Iran

[2] Islamic Azad Univ, Urmia Branch, Dept Chem, Orumiyeh, Iran

[3] Univ Wroclaw, Fac Chem, 14 Joliot Curie St, PL-50383 Wroclaw, Poland

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 01期

关键词：

STABILIZED PHOSPHORUS YLIDES; CATALYZED SYNTHESIS; AZIRIDINES; DIIODOMETHYLLITHIUM; DERIVATIVES; AMIDATION; PROTOCOL; REGIO; SCOPE; ARYL;

D O I：

10.1021/acs.orglett.8b03388

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, one-pot, and convenient approach for the reaction of the same precursors, trialkyl(aryl) phosphines, acetylene diesters, and benzhydroxamic acids has been developed to produce two important classes of heterocyclic compounds: N-benzoylaziridines and 1,4,2-dioxazoles. The strategy utilizes the intermediate solvation as a key step in product selectivity. The usefulness of the developed approach has been confirmed in the unprecedented highly cis-selective formation of the N-benzoylaziridines. In addition, the procedure provides a green alternative method for the synthesis of 1,4,2-dioxazoles employing beta-cyclodextrin nanoreactor in aqueous media.

引用

页码：22 / 26

页数：5

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