XJIPC OpenIR  > 资源化学研究室
Thesis Advisor卢崇道
Degree Grantor中国科学院大学
Place of Conferral北京
Degree Name硕士
Degree Discipline有机化学
KeywordBrook重排 三组分反应 Α-季碳-α-羟基-β-氨基酸酯


Other Abstract
α-Quaternary α-hydroxyl-β-amino esters are important building blocks in natural products and biologically active agents, such structures have anticancer, anti-Gram-positive and -negative bacteria activity. General and straightforward method for enantioselective synthesis of α-quaternary α-hydroxyl-β-aminoesters are badly needed but seldom reported. This thesis describes an efficient method for the enantioselective synthesis of α-quaternary α-hydroxyl-β-aminoesters via Brook rearrangement-mediated three-component reactions. We have developed a novel three-component coupling reaction of aryl Grignard reagents, silyl glyoxylates and N-tert-butanesulfinyl imines for constructing α-aryl-α-hydroxyl-β-aminoesters. These reactions exhibit excellent yields (up to 98%) and outstanding diastereoselectivity (dr > 20:1:0:0). By replacing the Grignard reagent with other organometallic reagents, we have developed a new method for the synthesis of α-methyl-α-hydroxyl-β-aminoesters by employing methyllithium. These reactions also display excellent yields (up to 93%) and outstanding diastereoselectivity (dr > 20:1:0:0). In addition,using N-tert-butanesulfinyl imines derived from acetophenons led to α-hydroxy-β-amino esterspossessing vicinal stereogenic quaternary carbon centersin in good yield with excellent diastereoselectivity. It is noted that the reactions induced by the different metal reagents with the same absolute configuration of chiral N-tert-butanesulfinyl imines would give different absolute configuration of the products. We propose and discussed the possible stereocontrolled pathway of the reactions through the stereochemical outcome of products.
Document Type学位论文
Recommended Citation
GB/T 7714
蒋九龙. Brook重排介导的三组分反应对手性α-季碳-α-羟基-β-氨基酸酯类化合物的合成研究[D]. 北京. 中国科学院大学,2014.
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