Stable Chiral Ligation for Asymmetric Organoborane Conversions via 10-(Trimethylsilyl)-9-borabicycloÔ3.3.2Òdecanes

本研究的目的是开发一类用于有机合成的新型有机硼手性助剂。该试剂来自蒎烯，这是一种储量丰富、价格低廉的“手性池”材料。本课程将探讨其在各种不对称反应中的潜在应用，包括羟醛反应、烯丙基化反应和硼氢化反应。待探索的其他可能的应用包括醛的不对称炔基硼反应，这可以得到光学活性的炔丙醇。通过这一奖项，有机和高分子化学项目支持波多黎各大学里约皮德拉斯分校化学系约翰·A·索德奎斯特博士的研究。索德奎斯特教授的研究是生产手性分子的重要领域，手性分子作为药物制剂一直是非常重要的。索德奎斯特博士采用的方法是用品烯作为天然的手性模板，用硼化学来调节手性从品烯到正在形成的分子的转移。

The objective of the proposed research is to develop a new class of organoboron chiral auxiliaries for use in organic synthesis. The reagent is derived from pinene, a plentiful and inexpensive "chiral pool" material. Potential applications to a variety of asymmetric reactions will be explored, including the aldol, allylation and hydroboration reactions. Other possible applications to be explored include asymmetric alkynylborations of aldehydes, which give optically active propargyl alcohols. 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, Rio Piedras. Professor Soderquist's research is in the important area of producing chiral molecules, which are ever-important as pharmaceutical agents. The method that is employed by Dr. Soderquist uses pinene as a natural chiral template, and boron chemistry to mediate the transfer of chirality from the pinene into the molecule that is being formed.