Proline Hydantoin Derivatives as Dual Purpose Chiral Auxiliary and Chiral Catalyst Precursors

许多有机分子可以以左手或右手形式存在。虽然这些分子除了互为镜像外，在所有方面都是相同的，但它们可能具有截然不同的化学和生理特性。公众在20世纪60年代开始意识到有机分子中的“惯用手性”，当时，人们将沙利度胺作为左旋和右旋的混合物给孕妇服用，以对抗晨吐。虽然这种药物的右旋形式是有益的，但左旋形式会导致儿童严重的出生缺陷，因此沙利度胺很快被禁止。随后，广泛的努力被放在有选择地以纯左手或右手形式合成有机分子上；这些努力今天仍在继续。拟议的研究概述了一种易于制造的分子片段的发展，当结合到特定的分子中时，为合成具有挑战性的“手性”分子提供了许多机会，无论是直接的，还是通过将其转化为催化剂。预计这一新片段将为开发新的化学转化提供机会，其中许多潜在的好处之一包括制备更安全的药物。*** *** **

Many organic molecules can exist in left or right-handed forms. While these molecules are identical in all respects except that they are mirror images of each other, they can have profoundly different chemical and physiological properties. The public became aware of the "handedness" in organic molecules in the 1960's when the drug thalidomide was given as a mixture of left and right-handed forms to pregnant women to combat morning sickness. Although the right-handed form of the drug was beneficial, the left-handed form caused severe birth defects in children, and thalidomide was quickly banned. Subsequently, extensive efforts were placed on synthesizing organic molecules selectively in purely left or right-handed forms; these efforts continue today. The proposed research outlines the development of an easy to make molecular fragment that, when incorporated into specific molecules, offers many opportunities for the synthesis of challenging to make "handed" molecules, either directly, or by its conversion into catalysts. It is anticipated this new fragment will offer opportunities to develop new chemical transformations, of which one of the many potential benefits includes the preparation of safer drugs.*** *** **