Asymmetric Synthesis with Boronic Esters

硼酸酯的不对称合成

• 批准号: 8922672
• 负责人: Donald Matteson
• 金额: --
• 依托单位: Washington State University
• 依托单位国家: 美国
• 项目类别: Continuing grant
• 财政年份: 1990
• 资助国家: 美国
• 起止时间: 1990-08-15 至 1993-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=8922672&HistoricalAwards=false
• 关键词: Asymmetric; Synthesis; Boronic; Esters

This research is being funded by the Organic Synthesis Chemistry Program. Dr. Matteson is developing new synthetic tools based upon the boron atom. This technique provides an extremely powerful way of controlling the relative stereochemistry of parts of a complex molecule. It will be very useful in preparing extremely pure pheromones needed in controlling insects. Directed asymmetric synthesis based on boronic ester chemistry has been found to be applicable to a wide variety of problems in natural product synthesis, and the proposed project will extend our basic knowledge of boronic ester chemistry and extend its applicability to new types of synthetic problems. To demonstrate and refine the features of the method that are already known, synthesisof several chiral insect pheromones will be undertaken. These provide significant but realistic synthetic challenges which will demonstrate some of the advantages of the approach, which is now theoretically capable of providing 1000:1 chiral isomer ratios of crude products The unequivocal stereochemistry and ability to produce all stereoisomers in highly pure form provided by this method should be useful for proving configurations of as yet unknown pheromones. New boronic ester chemistry will be investigated which has as its goal the connection of boronic esters produced via this chemistry with molecular fragments which may be obtained by other means, so that this chemistry can be applied more readily to the synthesis of highly complex natural products.

这项研究由有机合成化学计划资助。马特森博士正在开发基于硼原子的新合成工具。这种技术提供了一种非常有效的方法来控制复杂分子各部分的相对立体化学。这将是非常有用的，在制备控制昆虫所需的极纯信息素。基于硼酸酯化学的定向不对称合成已被发现适用于天然产物合成中的各种问题，并且所提出的项目将扩展我们对硼酸酯化学的基本知识并将其适用性扩展到新型合成问题。为了证明和完善已经知道的方法的特征，将进行几种手性昆虫信息素的合成。这些提供了显著但现实的合成挑战，这将证明该方法的一些优点，该方法现在理论上能够提供1000：1手性异构体比率的粗产物。该方法提供的明确的立体化学和以高纯度形式产生所有立体异构体的能力应该可用于证明尚未未知的信息素的构型。将研究新的硼酸酯化学，其目标是将通过这种化学产生的硼酸酯与可以通过其他手段获得的分子片段连接，使得这种化学可以更容易地应用于高度复杂的天然产物的合成。