Traceless chirality transfer from a norbornene β-amino acid to pyrimido[2,1-a]isoindole enantiomers

Q2 Chemistry

Tetrahedron, asymmetry Pub Date : 2017-10-15 DOI:10.1016/j.tetasy.2017.07.006

Ferenc Miklós , Kristóf Bozó , Zsolt Galla , Matti Haukka , Ferenc Fülöp

引用次数: 5

Abstract

The synthesis of two enantiomeric pairs of pyrimidoisoindoles 9a, 9b and 10a, 10b is reported. During a domino ring-closure reaction, followed by cycloreversion, the chirality of diendo-(−)-(1R,2S,3R,4S)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide [(−)-1] was successfully transfered to heterocycles (+)-9a, (+)-10a, (−)-9b, (−)-10b and (−)-10c.

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降冰片烯β-氨基酸到嘧啶[2,1-a]异吲哚对映体的无迹手性转移

报道了两对嘧啶异吲哚对映体9a, 9b和10a, 10b的合成。在多米诺骨牌环闭合反应中，双端-(−)-(1R,2S,3R,4S)-3-氨基双环[2.2.1]庚-5-烯-2-羧酰胺[(−)-1]的手性成功转移到杂环(+)-9a， (+)-10a，(−)-9b，(−)-10b和(−)-10c上。

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.