Williams David R, Plummer Scott V, Patnaik Samarjit
Department of Chemistry, Indiana University, Bloomington, IN 47405, United States.
Tetrahedron. 2011 Jul 8;67(27-28):5083-5097. doi: 10.1016/j.tet.2011.05.020.
Strategies for the stereocontrolled preparations of 2,6--and 2,6--substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in S' reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at -78 °C yield nonracemic 1,5-diols for chemoselective internal backside displacements. This concept is developed as a flexible and reliable strategy in studies toward leucascandrolide A macrolactone via the sequential applications of S' reactions leading to the C-C aldehyde , and the -tetrahydropyran , respectively.
已设计出立体控制制备2,6-和2,6-取代四氢吡喃的策略。这些研究探索了使用手性1,3,2-二氮杂硼烷控制剂在S'反应中进行不对称诱导的方法。在-78°C下与醛反应生成非外消旋的1,5-二醇，用于化学选择性内部背面取代。通过依次应用分别导致C-C醛和-四氢吡喃的S'反应，这一概念被发展成为一种灵活可靠的策略，用于对leucascandrolide A大环内酯的研究。
