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Taghizadeh, Mohammad Javad, Jadidi, Khosrow. (1394). Three-component procedure for the synthesis of new chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition. فصلنامه علمی زیست فناوری گیاهان زراعی, 3(Issue 2, pp. 72-147, Serial No. 7), 96-104.
Mohammad Javad Taghizadeh; Khosrow Jadidi. "Three-component procedure for the synthesis of new chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition". فصلنامه علمی زیست فناوری گیاهان زراعی, 3, Issue 2, pp. 72-147, Serial No. 7, 1394, 96-104.
Taghizadeh, Mohammad Javad, Jadidi, Khosrow. (1394). 'Three-component procedure for the synthesis of new chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition', فصلنامه علمی زیست فناوری گیاهان زراعی, 3(Issue 2, pp. 72-147, Serial No. 7), pp. 96-104.
Taghizadeh, Mohammad Javad, Jadidi, Khosrow. Three-component procedure for the synthesis of new chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition. فصلنامه علمی زیست فناوری گیاهان زراعی, 1394; 3(Issue 2, pp. 72-147, Serial No. 7): 96-104.

Three-component procedure for the synthesis of new chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition

Iranian chemical communication
مقاله 4، دوره 3، Issue 2, pp. 72-147, Serial No. 7، تیر 2015، صفحه 96-104    اصل مقاله (833.35 K)
نوع مقاله: Original Research Article
نویسندگان
Mohammad Javad Taghizadeh* 1؛ Khosrow Jadidi2
1Department of Chemistry, School of Sciences University of Imam Hossein, Tehran, Iran
2Department of Chemistry, Shahid Beheshti University, G.C. Tehran 1983963113, Iran
چکیده
The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imine)–Cu(II)triflate complex as catalyst.The reaction mechanism is discussedon the basis of the assignment of the absolute configuration of the cycloadducts.

The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imine)–Cu(II)triflate complex as catalyst.The reaction mechanism is discussedon the basis of the assignment of the absolute configuration of the cycloadducts.
کلیدواژه‌ها
Chiral auxiliaries؛ chiral spiro-oxindolopyrrolizidines؛ asymmetric 1-3-dipolar؛ azomethineylide
مراجع
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[6]  M.J. Taghizadeh,H. Arvinnezhad, S. Samadi, K. Jadidi, A. Javidan, B. Notash, Tetrahedron Letters, 2012, 53, 5148-5150.

[7]  M. Moemeni, H. Arvinnezhad, S. Samadi, M. Tajbakhsh, K. Jadidi, H.R. Khavasi, J. Heterocycl. Chem., 2012, 49, 190-194.

[8] S. Cabrera, R.G. Arrayás, J.C. Carretero, J. Am. Chem. Soc., 2005, 127, 16394-16395.

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[10] R. Breinbauer, E.N. Jacobsen, Angew. Chem. Int. Ed., 2000, 39, 3604-3607.

[11] K.V. Gothelf, K.A. Jorgensen, Chem. Rev., 1998, 98, 863-909.

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