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Issue 5, 2012
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Densely substituted unnatural L- and D-prolines as catalysts for highly enantioselective stereodivergent (3 + 2) cycloadditions and aldol reactions

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Abstract

(3 + 2) Cycloaddition reaction between azomethine ylides and π-deficient alkenes leads to densely substituted L- and D-unnatural prolines. These (3 + 2) cycloadducts in turn catalyse the preparation of an offspring of unnatural endo- and exo-L-proline derivatives. These latter compounds are also efficient catalysts of aldol reactions and yield aldol adducts with the opposite stereochemistry obtained under natural L-Pro organocatalysis.

Graphical abstract: Densely substituted unnatural l- and d-prolines as catalysts for highly enantioselective stereodivergent (3 + 2) cycloadditions and aldol reactions

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Publication details

The article was received on 17 Feb 2012, accepted on 21 Feb 2012 and first published on 22 Feb 2012


Article type: Edge Article
DOI: 10.1039/C2SC20199B
Citation: Chem. Sci., 2012,3, 1486-1491
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    Densely substituted unnatural L- and D-prolines as catalysts for highly enantioselective stereodivergent (3 + 2) cycloadditions and aldol reactions

    E. Conde, D. Bello, A. de Cózar, M. Sánchez, M. A. Vázquez and F. P. Cossío, Chem. Sci., 2012, 3, 1486
    DOI: 10.1039/C2SC20199B

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