A study of the diels-alder reaction of 3-oxabicyclo[3.3.0]oct-1(5)-ene-2,4-dione with cyclopentadiene and some related dienes
作者:P. Camps、J. Castañé、M. Feliz、M. Figueredo
DOI:10.1016/s0040-4020(01)91277-3
日期:1984.1
stereoselectivity in the last reaction. Steric factors seem to be responsible for the absence of reaction between 2 and 4. The analysis of the 13C NMR spectra of these adducts and some derived compounds confirms the tentative configuration assignment carried out on the basis of PMR data. Also, the synthesis of dimethyl(1R,2S,6R,7S)-10-oxotricy-clo [5.2.1.02.6]decane2,6-decarboxylate, 1, from the endo-adduct
3-氧杂双环[3.3.0]辛-1-(5)烯-2,4-二酮2与环戊二烯3、5,5-二乙氧基环戊二烯4和6,6-二甲基富勒烯5的反应是研究过。的反应2倍3的产率的预期内切-adduct,而反应2和5给出的混合物中内切-和外切-adducts其比例是略微依赖于反应条件。在过渡态下导致外向的有吸引力的静电相互作用-加合物可以解释在最后的反应中没有内在立体选择性。立体因素似乎是造成2和4之间没有反应的原因。这些加合物和某些衍生化合物的13 C NMR光谱分析证实了基于PMR数据进行的暂定构型分配。另外,描述了由2和5的反应的内加成物合成二甲基(1R,2S,6R,7S)-10-氧合-闭[5.2.1.0 2.6 ]癸烷2,6-脱羧酯1。