Organocatalytic Enantioselective 1,6-aza-Michael Addition of Isoxazolin-5-ones to p-Quinone Methides

被引：39

作者：

Toran, Ricardo ^{[1
]}

Vila, Carlos ^{[1
]}

Sanz-Marco, Amparo ^{[1
]}

Munoz, M. Carmen ^{[2
]}

Pedro, Jose R. ^{[1
]}

Blay, Gonzalo ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, C Dr Moliner 50, E-46100 Burjassot, Valencia, Spain

[2] Univ Politecn Valencia, Dept Fis Aplicada, Valencia 46071, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 05期

关键词：

Asymmetric catalysis; Enantioselectivity; Conjugate addition; Heterocycles; Alkylation; ASYMMETRIC 1,6-CONJUGATE ADDITION; ISOXAZOLONE BASED INHIBITORS; ACID-ESTERS; AMINO-ACIDS; ALKYLATION; ADDITION/AROMATIZATION; ISOXAZOL-5-ONES; ISOXAZOLINONES; NUCLEOPHILES; LACTONES;

D O I：

10.1002/ejoc.201901907

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A thiourea-Bronsted base bifunctional catalyst allowed the enantioselective 1,6-aza-Michael addition of isoxazolin-5-ones to p-quinone methides to give isoxazolin-5-ones having a chiral diarylmethyl moiety attached to the N atom with fair to good yields and enantiomeric excesses. To the best of our knowledge this reaction represents the first example of enantioselective N-alkylation of isoxazolin-5-ones as well as the first example of enantioselective 1,6-aza-Michael reaction involving p-quinone methides.

引用

页码：627 / 630

页数：4

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