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Issue 9, 2013
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Enantioselective construction of 2,5-dihydropyrrole skeleton with quaternary stereogenic center via catalytic asymmetric 1,3-dipolar cycloaddition involving α-arylglycine esters

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Abstract

A catalytic asymmetric construction of synthetically and biologically important 2,5-dihydropyrrole scaffolds with concomitant creation of multiple chiral carbon centers including one quaternary stereogenic center in high yields (up to 99%) and excellent enantioselectivities (up to 99% ee) has been established via an organocatalytic 1,3-dipolar cycloaddition using α-arylglycine esters as azomethine precursors. Moreover, a detailed investigation has been performed on the catalytic asymmetric 1,3-dipolar cycloadditions of α-arylglycine ester-generated azomethine ylides with alkynes, providing an efficient way to simultaneously access both 2,5-dihydropyrrole diastereomers in good enantioselectivities.

Graphical abstract: Enantioselective construction of 2,5-dihydropyrrole skeleton with quaternary stereogenic center via catalytic asymmetric 1,3-dipolar cycloaddition involving α-arylglycine esters

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Publication details

The article was received on 08 Aug 2012, accepted on 02 Jan 2013 and first published on 03 Jan 2013


Article type: Paper
DOI: 10.1039/C2OB26566D
Citation: Org. Biomol. Chem., 2013,11, 1482-1489
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    Enantioselective construction of 2,5-dihydropyrrole skeleton with quaternary stereogenic center via catalytic asymmetric 1,3-dipolar cycloaddition involving α-arylglycine esters

    F. Shi, G. Xing, W. Tan, R. Zhu and S. Tu, Org. Biomol. Chem., 2013, 11, 1482
    DOI: 10.1039/C2OB26566D

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