Study On Asymmetric Michael Addition Reaction Of N-Boc-α-amino-arylethanone With Cinnamaldehyde And 1,6-conjugation Addition Of Methylene Benzoquinone Compounds With Indole

This thesis is mainly composed of two parts: 1 、 Asymmetric Michael reaction of N-Boc-α-Amino-arylethanone and Cinnamaldehyde catalyted by Diarylprolinol silyl ethersDiarylprolinol silyl ethers have been widely used as efficient catalysts in a variety of catalytic asymmetric reactions,and achieved remarkable results such as Michael reaction.What’s more,the catalytic asymmetric Michael reaction of α,β-unsaturated aldehydes is a powerful and versatile carbon-carbon bond-forming process in organic synthesis.It has been found that α-amino-ketones act as donor in the Michael addition.Herein,we investigate the diarylprolinol silyl ethers to catalyze Michael reaction of N-Boc-α-Amino-arylethanone and α,β-unsaturated aldehyde,then the intermediate products are oxidized by PCC,affording expected product.After study on the effect of the types and amounts of catalysts,solvent,temperature,additives and other conditions on catalytic performance,the optimum reaction conditions were determined.Finally,We further studied the scope of application for the substrate α-Amino-aryl Ethanone under the optimal conditions,obtaining good yields up to 85% with excellent enantioselectivity up to 98%.The value of dr up to >99:1.(?)2、p-Toluenesulfonic acid-catalyzed 1,6-addition arylation of para-quinone methides(p-QMs)with IndolesPara-Quinone methides have been very extensive application in organic material and biological chemistry.It has a special structure,which leads it to be a electron acceptor in Michael addition reaction.Indole is a very active substance.which is a strong donor potential in the Michael addition.Heren,we study that p-Toluenesulfonic acid can catalysize 1,6-conjugated reactions of indoles and the para-Quinone methides,which can generate with three aryl chiral center of material.Based on the research of amount of catalysts,and reaction temperature,we obtained the optimum reaction conditions.Under the optimum conditions,the scope of reaction is explored with good yields up to 98%.(?)...