Carbon-Carbon Bond-Forming Reactions: Application to the Selective Synthesis of Alkenols and Cyclic Ethers

这项研究由大卫W.汤普森将由 威廉学院合成有机化学课程 还有玛丽 这项研究将主要由 本科生，并应提供训练有素的学生 他们参与了新的有机金属化合物的新发展， 化学. 研究的总目标是发展 3-亚烷基四氢呋喃的选择性合成， 5，6-二氢-2H-吡喃，以及三-和四-取代的烯丙基 和高烯丙醇。 环醚的合成 有两种类型：1） 有机钛/锆-铝碳代甲烷 炔属缩醛，然后是乙烯基金属/氧代碳正离子 偶联，和2）刘易斯酸促进的阳离子环化 炔缩醛 将特别强调 3-亚烷基四氢呋喃的选择性合成， 经受更新的醚裂解试剂， 选择性地产生三-/四-取代的烯醇。

This research by Dr. David W. Thompson will be funded by the Synthetic Organic Chemistry Program at the College of William and Mary. The research will be carried out primarily by undergraduate students and should provide well trained students who have been involved in new development of new organometallic chemistry. The general goal of the research centers on the development of selective syntheses for 3-alkylidenetetrahydrofurans, 5,6-dihydro-2H-pyrans, and tri- and tetra-substituted allylic and homoallylic alcohols. The projected cyclic ether syntheses are of two types: 1) bimetallic organotitanium/zirconium-aluminum carbometallation of acetylenic acetals followed by vinylmetal/oxocarbocation coupling, and 2) Lewis acid promoted cationic cyclization of acetylenic acetals. Particular emphasis will be placed on the selective synthesis of 3-alkylidenetetrahydrofurans which will be subjected to newer ether cleavage reagents with expectation of producing selectively tri-/tetra-substituted alkenols.