Abstract
We report the preparation of a range of N -protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poor ees, the structural variation together with the X-ray crystallographic study of the intra- and intermolecular hydrogen bonding reported suggest that the C 2 -symmetric catalysts are lead compounds for the further development of this methodology. • N -protected amino acid derived guanidine organocatalysts were prepared.. • A Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene was achieved in 26% ee. • X-ray analysis suggested strong intramolecular H-bonds between carbamate carbonyls and guanidine N-H’s.
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