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    • 57. 发明授权
    • Combination approach to chiral reagents or catalysts having amine or amino alcohol ligands
    • 具有胺或氨基醇配体的手性试剂或催化剂的组合方法
    • US06602817B1
    • 2003-08-05
    • US09425498
    • 1999-10-22
    • Nicos A. Petasis
    • Nicos A. Petasis
    • B01J3100
    • B01J31/2243B01J31/1805B01J31/223B01J2219/00738B01J2219/00745B01J2219/00747B01J2531/10B01J2531/20B01J2531/30B01J2531/40B01J2531/82B01J2531/84C07B53/00C07B2200/07C07C215/28C07C215/30C07C215/50C07C229/36C07D307/52C07K5/06026C40B30/08C40B40/18
    • Functionalized amine derivatives are prepared by reacting an amine, a carbonyl derivative, and an organoboron compound under mild conditions. Organoboronic acids react with amines and alpha-hydroxy aldehydes to give anti-alpha-amino alcohols with very high diastereoselectivities (>99% de). When optically pure alpha-hydroxy aldehydes are used in this process, no racemization occurs and the products are obtained with very high enantioselectivities (>99% ee). The reaction also works with unprotected glyceraldehyde to give the corresponding amino diol derivatives, while unprotected carbohydrates give the corresponding amino polyols. The chiral amino alcohol products of this process or their derivatives, react further with metals or non-metals to give adducts that are effective catalysts for a variety of asymmetric reactions. Overall, the present invention relies on the facile synthesis of the chiral amino alcohol ligands for the rapid construction of combinatorial libraries of chiral catalysts. These libraries can then be used to identify the most suitable catalyst for a particular asymmetric transformation.
    • 官能化胺衍生物通过在温和条件下使胺,羰基衍生物和有机硼化合物反应来制备。 有机硼酸与胺和α-羟基醛反应得到具有非常高的非对映选择性(> 99%de)的抗α-氨基醇。 当在该方法中使用光学纯的α-羟基醛时,不会发生外消旋化,并且以非常高的对映选择性(> 99%ee)获得产物。 该反应也适用于未保护的甘油醛,得到相应的氨基二醇衍生物,而未保护的碳水化合物则得到相应的氨基多元醇。 该方法的手性氨基醇产物或其衍生物进一步与金属或非金属反应,得到作为各种不对称反应的有效催化剂的加合物。 总之,本发明依赖于手性氨基醇配体的容易合成,用于快速构建手性催化剂组合文库。 然后可以使用这些文库来识别用于特定不对称转化的最合适的催化剂。