Halvorsen Geoff T, Roush William R
Department of Chemistry and Biochemistry, Scripps-Florida, Jupiter, Florida 33458, USA.
Org Lett. 2007 May 24;9(11):2243-6. doi: 10.1021/ol070858u. Epub 2007 May 5.
The synthesis of siloxacyclopentene-constrained trienes 7 and 10 and studies of their IMDA cycloadditions are described. The use of appropriately chosen thermal or Lewis acid conditions allows for cycloadducts 3-6 to be obtained with high levels of diastereoselectivity. These adducts possess trans-relationships between the hydroxyl group and the adjacent ring fusion proton, a stereochemical relationship not previously attainable in IMDA reactions.
本文描述了硅氧杂环戊烯受限三烯7和10的合成及其IMDA环加成反应的研究。使用适当选择的热条件或路易斯酸条件,可以以高非对映选择性获得环加成产物3-6。这些加合物在羟基与相邻环稠合质子之间具有反式关系,这是IMDA反应中以前无法实现的立体化学关系。