【作者】 丁娟；

【导师】 沈宗旋；

【作者基本信息】 苏州大学 ， 有机化学， 2006， 硕士

【摘要】 一、手性有机小分子催化剂催化的苯乙炔的不对称加成反应1.1手性氨基醇( S ) -2- ( 1-苄基四氢吡咯基)二苯基甲醇,生物碱辛可宁催化的苯乙炔与酮的不对称加成反应从天然氨基酸( S ) -脯氨酸合成的手性氨基醇( S ) -2- ( 1-苄基四氢吡咯基)二苯基甲醇,及生物碱辛可宁作为促进剂,用于苯乙炔对酮的对映选择性加成反应,得到较好产率(最高达89 %)和中等ee值(最高达77.9 %)的炔丙醇,加入Ti (OPri) 4可明显提高反应的对映选择性。1.2联萘酚催化的苯乙炔与α-酮酯的不对称加成反应以简单的联萘酚催化苯乙炔与α-酮酯的不对称加成反应,反应的产率及ee都不高,产率为:35.7 %,ee值为:7.7 %。二、手性C2对称硫脲催化剂的设计及合成我们从天然的氨基酸( S ) -脯氨酸出发通过几种方法合成手性的C2对称硫脲,并比较了合成路线的优异性。三、利用高效液相色谱测定不对称反应产物的E.E值更多还原

【Abstract】 1. The Asymmetric Addition of Phenylacetylene Catalyzed by Chiral Organic Catalysts 1.1 A Chiral Amino Alcohol,( S ) - ( 1-benzylpyrrolidin-2-yl ) -diphenylmethanol, and Cinchonine Were Evaluated As Promotors in The Asymmetric Additions of Phenylacetylene to Ketones ( S ) - ( 1-benzylpyrrolidin-2-yl ) -diphenylmethanol, a chiral amino alcohol prepared from ( S ) -proline, and cinchonine, were evaluated as promotors in the asymmetric additions of phenylacetylene to ketones, providing chiral propargylic alcohols with good yields ( up to 89 % ) and moderate enantioselectivities ( up to 77.9 % ee ) Adding Ti (OPri) 4 can lead to significant increase in the enantioselectivity of the reaction. 1.2. The Addition of Phenylacetylene toα-keto ester Catalyzed by BINOL BINOL was evaluated as promotors in the asymmetric additions of phenylacetylene toα-keto ester, providing chiral propargylic alcohols derivations. The low yields (up to 35.7 %) and ee (7.7 %) were obtained2. The Design and Synthesis of Chiral C2 Symmetry Thiourea A chiral C2 symmetry thiourea catalyst was prepared from (S) -proline, and different synthesis methods were discussed.3. Enatiomeric Excess of Asymmetric Reaction Products was detected by HPLC更多还原