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Synthesis of Bifunctional L-Prolinamide Derivative Organocatalysts

Author: LiJinYe
Tutor: GongYueFa；WangWeiZhou
School: Huazhong University of Science and Technology
Course: Organic Chemistry
Keywords: Asymmetric Catalysis The organic catalyst of the L - prolinamide Dual function Synthesis
CLC: TQ226.3
Type: Master's thesis
Year: 2007
Downloads: 137
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Abstract


Since 2000 , Barbas and List reported that L-proline can be efficient catalytic enantioselectivity aldol condensation reaction since the amount of L- proline derivative is synthesized , which comprises the amide derivative of L-prolinamide these catalysts are widely applied to the enantioselective aldol reaction , Michael addition reaction and Mannich reaction . The recent catalyst Some simply 2mol% of the amount can be obtained by gt; 99 ? Made such a huge step forward , but most of the catalyst on the dependence of the reaction substrates . Recently , a combination of Lewis acid and Lewis base have made new progress in asymmetric catalysis . In this paper, L-proline as the raw material, after esterification , aminolysis , condensed three-step reaction synthesis of the one end to the other end of the organic bases for the dual function of the Lewis acid L-proline amides organic catalyst . (1) L- proline methyl ester . In methanol as the solvent at room temperature under the conditions of L-proline methyl ester was synthesized by the reaction of L-proline with thionyl a yield of 83.2% . (2) N - ( 2 - aminoethyl ) - L - prolinamide of the synthesis. Synthesis of N-(2 - aminoethyl )-L- prolinamide in methanol as solvent, at room temperature conditions , the hydrolysis reaction by the L-proline methyl ester with excess ( 5 fold) ethylenediamine ammonia , produced was 80.0%. (3) bi-functional L - prolinamide class of organic synthesis of the catalyst 1 . In dichloromethane as the solvent under ambient conditions , was synthesized by a condensation reaction of N - ( 2 - aminoethyl ) - L - prolyl amide with salicylaldehyde target product in a yield of 27.5% . (4) the organic catalyst of the bi-functional L-prolyl amides 2 synthesis. In dichloromethane as solvent, at room temperature conditions , the N - ( 2 - aminoethyl ) -L - prolinamide and 3 , 5 - di-tert-butyl- salicylaldehyde condensation synthesis of the target product , yield 31.0% . Further, in the present experiments found that: in addition to the target product 1 and 2 , the secondary amine group on the pyrrole ring also with salicylaldehyde / 3 , 5 - di-tert - butyl - salicylaldehyde condensation reaction occurs , generating a dual- heterocyclic the novel compounds .

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CLC: > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of aliphatic compounds ( acyclic compounds) > Aliphatic nitrogen-containing compounds > Aliphatic amines and their derivatives
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