Abstract
This thesis dealt with the development of novel organocatalyst 35 which is derived from the coupling of trans-4-hydroxy-L-proline and N-phenyl-camphorsulfonamide. Organocatalyst 35 is proven to be a powerful catalyst (5 mol% loading) for the asymmetric Michael reaction of isobutyraldehyde to nitroalkenes with high chemical yields (up to 99%) and enantioselectivities (up to 95%). Treatment of α-substituted aldehyde with trans-β-nitrostyrene in the presence of 1-5 mol% organocatalyst 35 and 1-5 mol% p-nitrobenzoic acid generated synthetically useful chiral γ-nitroaldehyde with high chemical yields and excellent enantio-(98-99%) and diastereoselectivities(86/14 – 99.6/0.4).