不对称合成反应教材编辑.pptVIP

不对称合成反应;;;;手性是自然界的基本属性; ;内容;不对称合成;手性分子的费歇尔命名规则;Cahn-Ingold-Prelog命名规则;不对称和非对称;对映体和非对映体;(e.e.)和(d.e.) ;潜手性面，Re和Si面;二、手性的重要性;手性药物; 2、两种对映体药性相反; 3、其中一种有毒或引起严重副反应;手性农药;其他领域;海葵毒素;三、手性的发展历史;In 1894?，Hermann Emil Fischer?outlined the concept of?asymmetric induction;in which he correctly ascribed selective the formation of?D-glucose by plants to be due to the influence of optically active substances within chlorophyll. Fischer also successfully performed what would now be regarded as the first example of enantioselective synthesis, by enantioselectively elongating sugars via a process which would eventually become the?Kiliani–Fischer synthesis. ;However, the first enantioselective synthesis is often attributed to Willy Marckwald; who in 1904 described the enantioselective ?decarboxylation?of the?malonic acid?2-ethyl-2-methylmalonic acid, mediated by?brucine.;1905–1965;It was not until the 1950s that major progress really began. Driven in part by chemists such as?R. B. Woodward?and?Vladimir Prelog?but also by the development of new techniques. The first of these was?Xray Crystallography, which was used to determine the?absolute configuration?of an organic compound by?Johannes Bijvoet?in 1951.?Chiral chromatography was introduced a year later by Dalgliesh, who used?paper chromatography?to separate chiral amino acids.?Although Dalgliesh was not the first to observe such separations, he correctly attributed the separation of enantiomers to differential retention by the chiral cellulose. This was expanded upon in 1960, when Klem and Reed first reported the use of chirally-modified silica gel for chiralHPLC?chromatographic separation. ;Thalidomide;since 1965;Metal catalysed enantioselective synthesis was pioneered by?William S. Knowles,?Ryōji Noyori?and?K. Barry Sharpless; for which they would receive the 2001Nobel Prize in Chemistry.Knowles and Noyori began with the development of?asymmetric hydrogenation, which they developed independently in 1968. Knowles replaced the achira