Synthesis, resolution and applications of 3,3'-disubstituted BIPHEP and BINAP derivatives in asymmetric organic synthesis

3,3-二取代BIPHEP和BINAP衍生物的合成、拆分及其在不对称有机合成中的应用

基本信息

批准号：
335648-2005
负责人：
Keay, Brian
金额：
$ 1.09万
依托单位：
University of Calgary
依托单位国家：
加拿大
项目类别：
Collaborative Research and Development Grants
财政年份：
2008
资助国家：
加拿大
起止时间：
2008-01-01 至 2009-12-31
项目状态：
已结题

来源：
https://www.nserc-crsng.gc.ca/ase-oro/Details-Detailles_eng.asp?id=398965
关键词：
Synthesis resolution applications disubstituted BIPHEP

项目摘要

The goal of this proposal is to develop new asymmetric catalysts and reagents that will provide products of reactions with high enantioselectivity. Compounds that are marketed as drugs that contain one or more stereogenic centres can exist as two enantiomers. It is important that chemists design new asymmetric catalysts that allows for the production of one enantiomer selectively over the other as each enantiomer can behave differently within a chiral environment like the human body. Thus in order to market a new drug containing stereogenic centres, each anantiomer must be synthesized independent of the other and tested separately for unwanted side effects. This is not an easy task as enantiomers have the same chemical and physical properties in a non-chiral environment (i.e in the laboratory where they are synthesized). Thus chemists must design new asymmetric catalysts that allow for the formation of one enantiomer over the other in the laboratory. The design of catalysts outlined in this proposal should allow for the production of enantiomers selectively. By having to avoid a resolution, the cost of making the drug should be lower and thus ultimately the consumer should pay less for their prescriptions. Thus this research could ultimately benefit anyone needing drugs that contain stereogenic centres.

该提案的目标是开发新的不对称催化剂和试剂，以提供具有高对映选择性的反应产物。作为含有一个或多个立体中心的药物销售的化合物可以以两种对映异构体的形式存在。重要的是，化学家设计新的不对称催化剂，允许选择性地生产一种对映体而不是另一种对映体，因为每种对映体在人体等手性环境中可以表现不同。因此，为了将含有立体异构中心的新药推向市场，每种对映异构体必须独立于其他异构体进行合成，并单独测试不良副作用。这不是一件容易的事，因为对映体在非手性环境中（即在合成它们的实验室中）具有相同的化学和物理性质。因此，化学家必须设计新的不对称催化剂，以允许在实验室中形成一种对映体而不是另一种对映体。该提案中概述的催化剂设计应允许选择性地生产对映体。通过避免决议，生产药物的成本应该更低，因此最终消费者应该为处方支付更少的费用。因此，这项研究最终可能使任何需要含有立体中心的药物的人受益。