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

脯氨酸乙内酰脲衍生物作为双重用途的手性助剂和手性催化剂前体

• 批准号: RGPIN-2016-05081
• 负责人: Metallinos, Costa
• 金额: $ 2.19万
• 依托单位: Brock University
• 依托单位国家: 加拿大
• 项目类别: Discovery Grants Program - Individual
• 财政年份: 2022
• 资助国家: 加拿大
• 起止时间: 2022-01-01 至 2023-12-31
• 项目状态: 已结题
• 来源: https://www.nserc-crsng.gc.ca/ase-oro/Details-Detailles_eng.asp?id=748014
• 关键词: Proline; Hydantoin; Derivatives; Dual; Purpose

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.

许多有机分子可以以左手或右手形式存在。虽然这些分子在所有方面都是相同的，除了它们是彼此的镜像，但它们可以具有完全不同的化学和生理特性。在20世纪60年代，当药物沙利度胺以左手和右手形式的混合物给孕妇服用以对抗晨吐时，公众开始意识到有机分子的“手性”。虽然药物的右旋形式是有益的，左旋形式导致儿童严重的出生缺陷，沙利度胺很快被禁止。随后，人们进行了大量的努力，选择性地合成纯左手或右手形式的有机分子;这些努力一直持续到今天。拟议的研究概述了一种易于制造的分子片段的发展，当将其纳入特定分子时，为直接或通过转化为催化剂合成具有挑战性的“手”分子提供了许多机会。预计这种新的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。