Synthesis of trans,trans-2,3,4-trisubstituted chromans from 3-nitro-2Н-chromenes and enamines of acetoacetic ester and acetylacetone. A new type of configurationally stable atropisomers

被引：0

作者：

Vladislav Yu. Korotaev

Alexey Yu. Barkov

Marina A. Ezhikova

Mikhail I. Kodess

Vyacheslav Ya. Sosnovskikh

机构：

[1] Ural Federal University named after the first President of Russia B. N. Yeltsin,Institute of Natural Sciences

[2] Ural Branch of Russian Academy of Sciences,I. Ya. Postovsky Institute of Organic Synthesis,

来源：

Chemistry of Heterocyclic Compounds | 2015年 / 51卷

关键词：

chromans; 3-nitro-2; -chromenes; push-pull enamines; atropisomerism; nucleophilic addition;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

Enamines of acetoacetic ester and acetylacetone added at the activated double bond of 2-R1-3-nitro-2Н-chromenes (R1 = CF3, CCl3, Ph) with their central α-С atoms, forming trans,trans-2,3,4-trisubstituted chromans. The adducts obtained from acetylacetone enamines represented mixtures of comparable amounts of configurationally stable atropisomers, the formation of which was connected with hindered rotation around the C(sp3)–C(sp2) bond. A reaction with enamines of acetoacetic ester led practically exclusively to a single anti atropisomer.

引用

页码：531 / 540

页数：9

共 4 条

[1] Synthesis of trans,trans-2,3,4-trisubstituted chromans from 3-nitro-2H-chromenes and enamines of acetoacetic ester and acetylacetone. A new type of configurationally stable atropisomers
Korotaev, Vladislav Yu.
Barkov, Alexey Yu.
Ezhikova, Marina A.
Kodess, Mikhail I.
Sosnovskikh, Vyacheslav Ya.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (06) : 531 - 540
[2] Products from the addition of acetoacetic ester or acetylacetone to 3-nitro-2Н-chromenes – axially chiral trans,trans-2,3,4-trisubstituted chromans and related pyrazoles
Vladislav Yu. Korotaev
Igor B. Kutyashev
Alexey Yu. Barkov
Marina A. Ezhikova
Mikhail I. Kodess
Vyacheslav Ya. Sosnovskikh
Chemistry of Heterocyclic Compounds, 2015, 51 : 704 - 708
[3] Products from the addition of acetoacetic ester or acetylacetone to 3-nitro-2H-chromenes - axially chiral trans,trans-2,3,4-trisubstituted chromans and related pyrazoles
Korotaev, Vladislav Yu.
Kutyashev, Igor B.
Barkov, Alexey Yu.
Ezhikova, Marina A.
Kodess, Mikhail I.
Sosnovskikh, Vyacheslav Ya.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (08) : 704 - 708
[4] Synthesis of 2,3,4-trisubstituted chromans via nucleophilic addition of N-, C-, and S-nucleophiles to 3-nitro-2-trihalomethyl-2H-chromenes.: Stereochemical and conformational preferences
Korotaev, VY
Sosnovskikh, VY
Kutyashev, IB
Kodess, MI
LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (07) : 616 - 620

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