From cyclooctatetraene to chiral polyfunctionalized C8 building blocks—meso-persubstituted oxepanes and azepanes
作者:Joachim Armbruster、Frank Stelzer、Peter Landenberger、Christian Wieber、Dieter Hunkler、Manfred Keller、Horst Prinzbach
DOI:10.1016/s0040-4039(00)00905-9
日期:2000.7
Cyclooctatetraene—via its 1α,2α,5α,6α-diepoxy-3β,4β-diol (4)—is the basis for the construction of specifically polyfunctionalized C8 building blocks. Whilst with monofunctional nucleophiles only monosubstitution and with 1,1-dinucleophiles neatly intramolecular cyclization to aza(oxa,thia)bicyclo[4.2.1]nonenes occurred, the desired substitution pattern became, in principle, accessible with 1,2-disubstituted
环辛酸酯通过其1α,2α,5α,6α-二环氧-3β,4β-二醇(4)-是构建特定的多官能化C 8结构单元的基础。尽管单官能亲核试剂仅被单取代,而1,1-二亲核试剂却在分子内被环化成aza(oxa,thia)双环[4.2.1]壬烯,但所需的取代模式在原则上变得可与1,2-二取代的肼接触。7杂[4.2.1]的有用自行车的制备内消旋-persubstituted azepanes和oxepanes被例示。