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

Taghizadeh, Mohammad Javad; Jadidi, Khosrow

Document Type : Original Research Article

Authors

¹ Department of Chemistry, School of Sciences University of Imam Hossein, Tehran, Iran

² Department of Chemistry, Shahid Beheshti University, G.C. Tehran 1983963113, Iran

Abstract

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.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

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Iranian chemical communication

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

References

References

Volume 3, Issue 2, pp. 72-147, Serial No. 7
April 2015
Pages 96-104

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

References

References

Volume 3, Issue 2, pp. 72-147, Serial No. 7April 2015Pages 96-104

Volume 3, Issue 2, pp. 72-147, Serial No. 7
April 2015
Pages 96-104