Synthesis of 4-Phosphinylpyrrolidin-3-ones via [3+2] Cycloaddition of Nitrones with Phosphinylallenes

被引：3

作者：

Hammami, Rayhane ^{[1
,3
]}

Maldivi, Pascale ^{[2
]}

Philouze, Christian ^{[1
]}

Carret, Sebastien ^{[1
]}

Darses, Benjamin ^{[1
]}

Touil, Soufiane ^{[3
]}

Poisson, Jean-Francois ^{[1
]}

机构：

[1] Univ Grenoble Alpes, CNRS, DCM, F-38000 Grenoble, France

[2] Univ Grenoble Alpes, CEA, CNRS, IRIG SyMMES, F-38000 Grenoble, France

[3] Univ Carthage, Fac Sci Bizerte, Lab Heteroorgan Cpds & Nanostruct Mat, LR18ES11, Jarzouna 7021, Tunisia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 09期

关键词：

Nitrones; allenes; heterocycles; cycloaddition; rearrangement; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; HIV PROTEASE INHIBITORS; DIPOLAR CYCLOADDITION; ASYMMETRIC-SYNTHESIS; ALPHA; ACID; REARRANGEMENT; ALCOHOLS; ALLENES; OXIDES;

D O I：

10.1002/adsc.202201386

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A variety of 4-phosphinylpyrrolidin-3-ones was prepared via a [3+2] cycloaddition between aryl aldonitrones and phosphinylallenes. The products were isolated as unique 4,5-trans diastereomers, in yields between 47% and 80%, over 23 examples. In the case of chiral racemic allenes, a 2:1 to 4:1 moderate 2,5-diastereoselectivity was observed. Under the reaction conditions, the cycloadducts directly undergo a rearrangement to afford selectively the corresponding pyrrolidin-3-ones. DFT calculations provide some insights into the mechanism, involving the homolytic cleavage of the N-O bond of the cycloadduct.

引用

页码：1385 / 1390

页数：6

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