Asymmetric reactions in ionic liquids and water using organocatalysts
YANG HAIYAN
YANG HAIYAN
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Abstract
In this thesis, the atom-economic direct asymmetric organocatalytic aldol reaction and amine conjugate addition reaction in environmentally friendly solvents were developed: (1) Ionic liquid, 1-n-butyl-3-methylimidazolium hexafluorophosphate ([bmim] PF6) is a suitable solvent for proline-catalyzed asymmetric aldol reaction. Furthermore, the ionic liquid containing chiral catalyst L-proline can be reused without decrease in yield and selectivity. (2) Two kinds of new organocatalysts, exo-2-azabicyclo[2.2.1]heptane-3-carboxylic acid and dipeptides derived from L-proline, were developed. Exo-2-azabicyclo[2.2.1]heptane-3-carboxylic acid was found to be an efficient catalyst for direct asymmetric aldol reaction. The dipeptide-catalyzed aldol reaction in water gives the desired products with moderate enantioselectivity. (3) Conjugate addition of amines to I?, I?-ethylenic compounds were efficiently carried out in the environmentally friendly ionic liquid media under mild condition to provide an easy access to trifluoromethylated amines.
Keywords
environmentally friendly, ionic liquid, water, organocatalysis, asymmetric reaction.
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Date
2005-01-14
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Thesis