Exceptionally strong, neutral, enantiomerically-pure diamine bases

化学家将从另一个分子中接受或去除质子的分子称为“碱”，将提供质子的化合物称为“布朗斯台德酸”。质子的移除和添加在有机化学和生物化学中普遍存在，并且是许多合成操作的重要组成部分，化学家可以通过这些操作以合乎逻辑和有效的方式构建新的或已知的分子。中性有机分子的去质子化（通过碱除去质子）产生带负电荷的产物，被描述为“阴离子”。有机分子中碳原子的去质子化产生“碳负离子”，这通常作为合成过程的一部分进行，以便提供对其他另一种物质的必要反应性，从而允许形成新分子。许多有机分子是手性的，因此以两种镜像形式存在。对于批准、许可和处方，手性药物（> 99%是有机分子）通常必须制备为单一镜像形式。在没有任何形式的控制的情况下，化学反应提供了镜像的相等混合。因此，一种方法是将混合物分离成两种成分，称为拆分。另一种方法涉及使用精心设计或优化的化学控制系统，这些系统本身是手性的，并且影响路径，以便使其严重偏向一个镜像或另一个镜像。这种技术被称为不对称合成，并且总是需要新的方法来施加这种控制。该提案描述了一类新的碱的设计，我们提出将能够选择性地使有机分子去质子化，以便产生镜像产物的不等混合物，理想地比率> 99 / 1，从而为合成化学家提供用于控制反应的新的不对称合成工具。具有讽刺意味的是，所提出的工作的主要部分将涉及使用不对称合成领域中其他人开发的选择性金属催化剂来制备作为单镜像形式的新碱。当然，开发这些催化剂的工作人员并没有打算将它们用于制备这种碱，这一点证明了新的不对称方法的重要性-好处可能是广泛的，在某些方面是不可预测的。我们对新型手性碱体系的设计充满信心，并希望为社会提供大量、高效、广泛应用的试剂。

Chemists describe molecules that accept or remove a proton from another molecule as a 'base', and the compound that donates the proton as a 'Bronsted acid'. The removal and addition of protons is ubiquitous in organic and biological chemistry and is an essential part of many synthetic manipulations by which chemists can contruct new or known molecules in a logical and efficient manner. Deprotonation (removal of a proton by a base) of a neutral organic molecule generates a negatively charged product, described as an 'anion', Deprotonation at a carbon atom in an organic molecule generates a 'carbanion' and this is often conducted as part of a synthetic procedure so as to provide the requisite reactivity towards other another species, and thus allow the formation of new molecules. Many organic molecules are chiral ('handed') and thus exist in two mirror image forms. For approval, license and prescription, pharmaceuticals (>99 % of which are organic molecules) that are chiral must usually be prepared as a single mirror image form. In the absence of any form of control, chemical reactions afford an equal mixture of mirror images. One method thus involves separating the mixture into its two components, know as resolution. Another method involves using carefully designed or optimsed chemical control systems which are themselves chiral and that influence the path so as to bias it heavily towards one mirror image or the other. Such a technique is known as asymmetric synthesis and new methods to exert such control are always needed. This proposal describes the design of a new class of bases that we propose will be able to selectively deprotonate organic molecules so as to generate unequal mixtures of mirror image products, ideally in ratios > 99 / 1, thereby providing the synthetic chemist with a new asymmetric synthesis tool for control of reactions. The major part of the work proposed will, ironically, be involved in preparing the new bases as single mirror image forms, using selective metal catalysts developed by others in the field of asymmetric synthesis. Of course, the workers who developed these catalysts had no intention that they would be used to prepare such bases and this point demonstrates the importance of new asymmetric methods - the benefits can be wide and in some ways unpredictable. We are confident in the design of our novel chiral base systems and aspire to provide the community with a reagent that will be available in large quantity, be highly efficient, and thus widely applied.