СТЕРЕОНАПРАВЛЕННЫЙ СИНТЕЗ (E)- И (Z)-ИЗОМЕРОВ 8-ХЛОРОКТ-7-ЕН-4-ОНА
Аннотация
Для цитирования:
Шахмаев Р.Н., Сунагатуллина А.Ш., Алиева Р.М., Зорин В.В. Стереонаправленный синтез (E)- и (Z)-изомеров 8-хлорокт-7-ен-4-она. Изв. вузов. Химия и хим. технология. 2017. Т. 60. Вып. 1. С. 40-44.
С использованием селективного твердофазного моноалкилирования этил-3-оксогекса-ноата индивидуальными изомерами 1,3-дихлорпропена и последующего декарбалкоксилирования образующихся хлорвинилпроизводных в оптимизированных условиях Крапчо разработан эффективный метод синтеза изомерно чистых (E)- и (Z)-8-хлорокт-7-ен-4-онов.
Литература
Metal-Catalyzed Cross-Coupling Reactions. Ed. de Meijere A., Diederich F. N.-Y.: Wiley-VCH. 2004. 916 p.
Jeffery T. Recent Improvements and Developments in Heck Type Reactions and Their Potential in Organic Synthesis. Advances in Metal-Organic Chemistry. 1996. V. 5. P. 153-260.
Shakhmaev R.N., Ishbaeva A.U., Zorin V.V. Pd-Cataly-zed synthesis of 1-[(2E,4E)-dodeca-2,4-dienoyl]piperidine. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2011. V. 54. N 10. P. 97-99 (in Russian).
Shakhmaev R.N., Sunagatullina A.Sh., Zorin V.V. A new approach to the synthesis of ethyl (4E)-alkenoates. Zhurn. Obshcheiy Khimii. 2013. V. 83. N 11. P. 2018-2020. DOI: 10.1134/S1070363213110078.
Handbook of organopalladium chemistry for organic synthe-sis. Ed. E. Negishi. N.- Y.: Wiley interscince. 2002. 3424 p.
Izibaeva A.U., Shakhmaev R.N., Spirikhin L.V., Zorin V.V. Synthesis of methyl ester 2(Е), 4(Е)-dodecadienoic acid based on Heck reaction. Bash. Khim. Zhurn. 2009. V. 16. N 1. P. 30-31 (in Russian).
Negishi E., Huang Z., Wang G., Mohan S., Wang C., Hattori H. Recent Advances in Efficient and Selective Syn-thesis of Di-, Tri-, and Tetrasubstituted Alkenes via Pd-Catalyzed Alkenylation−Carbonyl Olefination Synergy. Acc. Chem. Res. 2008. V. 41. N 11. P. 1474-1485. DOI: 10.1021/ar800038e.
Ishbaeva A.U., Sunagatullina A.Sh., Shakhmaev R.N., Zorin V.V. Stereoselective synthesis of 1-[(2E,4E)-deca-2,4-dienoyl]piperidine. Bash. Khim. Zhurn. 2010. V. 17. N 3. P. 53-55 (in Russian).
Takhautdinova A.U., Mindiyarova E.R., Shakhmaev R.N., Zorin V.V. Reactions of (E)- and (Z)-1,3-dichloropropenes with secondary amines. Russ.J.Appl. Chem. 2011. V. 84. N 3. P. 504-506. DOI: 10.1134/S1070427211030293.
Sunagatullina A.Sh., Shakhmaev R.N., Zorin V.V. Syn-thesis of ethyl (4E)-tridec-4-ene-6-ynoate. Russ. J. Gen. Chem. 2013. V. 83. N 1. P. 148-149. DOI: 10.1134/S1070363213010313.
Shakhmaev R.N., Sunagatullina A.Sh., Zorin V.V. Ste-reoselective synthesis of allylamines by iron-catalyzed cross-coupling of 3-chloroprop-2-en-1-amines with Grignard rea-gents. Synthesis of naftifine. Russ. J. Org. Chem. 2014. V. 50. N 3. P. 322-331. DOI: 10.1134/S1070428014030038.
Shakhmaev R.N., Sunagatullina A.Sh., Zorin V.V. Iron-catalyzed synthesis of cinnarizine. Russ.J. Org. Chem. 2015. V. 51. N 1. P. 95-97. DOI: 10.1134/S1070428015010169.
Sunagatullina A. Sh., Shakhmaev R.N., Zorin V.V. Al-kynilation of diethylmalonate by individual isomers of 1,3-dichloropropene in phase-transfer catalysis conditions. Bash. khim. zh. 2012. V. 19. N 2. P. 5-7 (in Russian).
Shakhmaev R.N., Sunagatullina A.Sh., Filippova E.A., Zorin V.V. Alkylation of ethyl 3-oxobutanoate by individual isomers of 1,3-dichloropropene in phase-transfer catalysis conditions. Bash. Khim. Zhurn. 2013. V. 20. N 1. P. 45-47 (in Russian).
Gonzalez A., Guell F., Marquet J., Moreno-Manas M. Alkylation of β-diketones through their Сo(II), Сo(III) and Zn(II) complexes. 1-Bromoadamantane as alkylating agent Tetrahedron Lett. 1985. V. 26. P. 3735-3738. DOI: 10.1016/S0040-4039(00)89236-9.
Clark J. H., Miller J. M. Hydrogen bonding in organic synthesis. Part 6. C-Alkylation of β-dicarbonyl compounds using tetra-alkylammonium fluorides. J. Chem. Soc., Perkin Trans. 1. 1977. P. 1743-1745. DOI: 10.1039/P19770001743.
Ranu B. C., Bhar S. Surface-mediated solid-phase reaction. Part 2. Highly selective mono- and di-C-alkylation of 1,3-dicarbonyl compounds on the surface of alumina. J. Chem. Soc., Perkin Trans. 1. 1992. P. 365-368. DOI: 10.1039/P19920000365.