Chiral amidate complexes for the diastereoselective and enantioselective synthesis of chiral amines and N-Heterocycles

用于手性胺和 N-杂环的非对映选择性和对映选择性合成的手性酰胺化物配合物

• 批准号: 381137-2009
• 负责人: Schafer, Laurel
• 金额: $ 7.29万
• 依托单位: University of British Columbia
• 依托单位国家: 加拿大
• 项目类别: Strategic Projects - Group
• 财政年份: 2011
• 资助国家: 加拿大
• 起止时间: 2011-01-01 至 2012-12-31
• 项目状态: 已结题
• 来源: https://www.nserc-crsng.gc.ca/ase-oro/Details-Detailles_eng.asp?id=484900
• 关键词: Chiral; amidate; complexes; diastereoselective; enantioselective

Catalytic methods afford energy efficient routes for the synthesis of complex molecules. Amines are critical building blocks for the assembly of a broad range of target compounds including alkaloid natural products, pharmaceuticals and agrochemicals. Often the required amine building blocks are chiral, meaning they have non-superimposable mirror images (enantiomers), and these enantiomers can have different properties when reacted with targeted biological receptors in human health treatments. Thus, the selective synthesis of enantiomeric amines and N-containing cyclic compounds (N-heterocycles) is an important aspect of daily production for the pharmaceutical industry. New methods to achieve the efficient syntheses of these small molecule building blocks can result in reduced waste production and cost savings during manufacture. The Schafer group has recently discovered a new family of catalysts for the efficient synthesis of chiral amines from simple amines and alkene feedstocks, in a 100% atom-economic reaction (there are no by-products in this reaction). This new reaction, the alpha-alkylation of amines, assembles the desired chiral amine products in only one step, with no by-products, by using a synthetic strategy that is complementary to traditional step-wise routes. A focused effort to realize the full potential of this new synthetic transformation and to extend academic achievements to small molecules of relevance to the pharmaceutical industry is supported by Boehringer Ingelheim Canada Ltd. This collaboration will exploit this emerging technology in the competitive manufacturing of required amine small molecules for the pharmaceutical industry. Using this catalytic

催化方法为复杂分子的合成提供了能量有效的途径。胺是组装广泛的目标化合物（包括生物碱天然产物、药物和农用化学品）的关键构件。通常所需的胺结构单元是手性的，这意味着它们具有不可重叠的镜像（对映异构体），并且这些对映异构体在与人类健康治疗中的靶向生物受体反应时可以具有不同的性质。因此，选择性合成对映体胺和含氮环状化合物（N-杂环）是制药工业日常生产的重要方面。实现这些小分子结构单元的有效合成的新方法可以减少制造过程中的废物产生并节省成本。Schafer集团最近发现了一种新的催化剂家族，用于在100%原子经济性反应中从简单胺和烯烃原料有效合成手性胺（该反应中没有副产物）。这种新的反应，胺的α-烷基化，通过使用与传统分步路线互补的合成策略，仅在一个步骤中组装所需的手性胺产物，没有副产物。Boehringer Ingelheim Canada Ltd.支持集中精力实现这种新合成转化的全部潜力，并将学术成果扩展到与制药行业相关的小分子。此次合作将利用这种新兴技术，为制药行业生产所需的胺小分子。利用这种催化剂