Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study?

RSC Advances Pub Date: 2020-06-11 DOI: 10.1039/C9RA07508A

Abstract

The preparation of a range of amino acid derived guanidine organocatalysts is reported together with their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 56%. Some insight into the mechanism was sought by using X-ray crystallography and a detailed study of the intra- and intermolecular hydrogen bonding is reported.

Graphical abstract: Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study
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