Novel Stable Chiral Ligation for Asymmetric Organoborane Conversions via 10-Substituted-9-borabicyclo[3.3.2]decanes

这项工作的目标涉及有机硼化学的几个方面。Soderquist教授和他的团队将首先制备一些手性烯丙基、丁基、烯丙基和炔基硼试剂，这些试剂含有9-硼比环[3.3.2]十烷骨架。烯丙基、丁基和烯丙基试剂将用于前手性醛和酮的不对称加成反应。手性炔基有机硼试剂将用于烯酮的不对称共轭加成反应。硼核磁共振将用于评估这些加成反应的立体选择性。有了这个奖项，有机和大分子化学项目支持波多黎各大学化学系的John A. Soderquist博士的研究。斯图尔特博士将致力于开发能够影响多种化学反应的有机硼试剂。这个小组将探索立体选择性加成反应，使用含有酮和醛的分子作为底物。这些加成反应产生的分子具有手性（具有两个不可重叠的镜像），并且只能形成两种可能形式中的一种（单一对映体）。这类反应的发展是当今制药工业面临的最重要问题之一。在这项工作过程中训练的学生将获得制药和特种化学品行业所需的技能，这些行业现在生产许多单一对映体化合物。

The objectives of this work involve several aspects of organoboron chemistry. Professor Soderquist and his group will first prepare a number of chiral allyl, crotyl, allenyl, and alkynyl boron reagents which contain the 9-borabicyclo[3.3.2]decane framework. The allyl, crotyl, and allenyl reagents will be utilized in asymmetric addition reactions to prochiral aldehydes and ketones. The chiral alkynyl organoboron reagents will be used in asymmetric conjugate addition reactions to enones. Boron NMR will be used to assess the stereoselectivities of these addition reactions. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. John A. Soderquist of the Department of Chemistry at the University of Puerto Rico. Dr. Stewart will work on the development of organoboron reagents capable of effecting a number of chemical reactions. This group will explore stereoselective addition reactions using molecules containing ketones and aldehydes as substrates. These addition reactions produce molecules which are chiral (have two nonsuperimposable mirror images) and make only one of the two possible forms (a single enantiomer). Development of this family of reactions is one of the most important problems facing the pharmaceutical industry today. Students trained during the course of this work will gain skills needed by the pharmaceutical and speciality chemicals industries which now produces a number of single enantiomer compounds.