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Developing an Understanding of Asymmetric Induction

加深对不对称感应的理解

基本信息

批准号：
8005177
负责人：
PATRICK J WALSH
金额：
$ 9.29万
依托单位：
UNIVERSITY OF PENNSYLVANIA
依托单位国家：
美国
项目类别：
财政年份：
2010
资助国家：
美国
起止时间：
2010-01-07 至 2010-12-31
项目状态：
已结题

项目摘要

DESCRIPTION (provided by applicant): The broad, long-term objectives of this proposal are to develop new synthetic methods that enable the preparation of important intermediates for organic and medicinal chemistry. Our methods make possible, for the first time, the large-scale synthesis of enantioenriched diarylmethanols from aryl bromides. This method will be applied to the synthesis of enantiomerically enriched heterocycles bearing important pharmacophores, such as furans and pyridines. We have also developed several new routes to pyranones, furanosidic aldehydes, furans, and pyrroles. These medicinally important heterocycles can be prepared with high enantioselectivities using our methods. We have developed one-pot synthesis of a-hydroxy ketones, allylic alcohols, and substituted cyclopropanes from a versatile 1-alkenyl-1,1-bimetallic intermediate. These methods will be useful in complex molecule synthesis. The Specific Aims of this proposal are: I. Development of Direct Methods for Conversion of Aryl, Vinyl, and Alkyl Bromides to Enantioenriched Alcohols. II. Introduction of New Methods For Heterocycle Syntheses. III: Development of 1-Alkenyl-1,1-Bimetallic Reagents for Complex Molecule Synthesis. This project presents new methods to synthesize important chiral building blocks that were not easily accessible, but find utility in health-related applications, particularly in the synthesis of enantioenriched pharmaceutical agents.

描述（由申请人提供）：本提案的广泛、长期目标是开发新的合成方法，以制备有机化学和药物化学的重要中间体。我们的方法使之成为可能，第一次，大规模合成对映体富集的二芳基甲醇从芳基溴。这种方法将被应用于合成富含对映异构体的具有重要药效团的杂环化合物，如呋喃和吡啶。我们还开发了几种合成吡喃酮、呋喃糖苷醛、呋喃和吡咯的新路线。这些重要的医药杂环可以用我们的方法制备高对映选择性。我们开发了一种从多用途的1-烯基-1，1-二烯丙基中间体一锅法合成α-羟基酮、烯丙醇和取代环丙烷的方法。这些方法在复杂分子的合成中具有重要的应用价值。本建议的具体目标是：一。芳基、乙烯基和烷基溴直接转化为对映体富集醇的方法的发展。二.杂环合成新方法介绍。III：用于合成复杂分子的1-烯基-1，1-双金属试剂的开发。该项目提出了合成重要的手性结构单元的新方法，这些结构单元不容易获得，但在与健康相关的应用中发现了实用性，特别是在合成对映体富集的药物制剂中。