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Title of article :
The organocatalytic enantioselective [3+2] cycloaddition reaction of α,β-unsaturated aldehydes with azomethine ylides applied to the asymmetric synthesis of densely substituted pyrroloisoquinolines
Author/Authors :
Ainara Iza، نويسنده , , Iratxe Ugarriza، نويسنده , , Uxue Uria، نويسنده , , Efra?m Reyes، نويسنده , , Luisa Carrillo، نويسنده , , Jose L. Vicario، نويسنده ,
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هفته نامه با شماره پیاپی سال 2013
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Abstract :
The synthesis of densely functionalized pyrrolo[2,1-a]isoquinolines was accomplished using the organocatalytic [3+2] cycloaddition between enals and azomethine ylides under iminium catalysis developed in our group some years ago as the key step. The cycloaddition proceeds smoothly yielding the corresponding pyrrolidine as a single endo diastereoisomer with enantiopurity in the range of 94–96% and further manipulations of the obtained cycloadducts using high yielding reaction protocols and a final mesylation/intramolecular N-alkylation sequence allowed the synthesis of target compounds in which the integrity of all stereocenters installed during the first step is maintained.
Keywords :
Cycloaddition , Pyrroloisoquinolines , Heterocycles , Dipolar reaction , Organocatalysis
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