Abstract
This thesis deals with the use of organocatalyst 75b, comprising of trans-4-TIPSO-L-proline and N-phenyl camphorsulfonamide skeletons, in the asymmetric Mannich reaction of α-silyloxyethanal to N-tosylimines, affording syn 1,2-amino alcohols with reasonable to good chemical yield (31% to 91%), slight to moderate diastereoselectivities (52:48 to 85:15) and moderate to good enatioselectivities (89 to >99% ee of the trans 89 products). An extensive and through screening on the solvents, additives and aldehyde equivalents identified that 5 mol % of the catalyst and 6 mol % of acid additive were able to efficiently provide 87% yield of the addition product with 97 % ee for the 4-methyl substituted example. Furthermore, it was found that the binary IPA-DCM solvent system was important for achieving good yields.