Adam Waldemar, Gogonas Efstathios P, Hadjiarapoglou Lazaros P
Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.
J Org Chem. 2003 Nov 14;68(23):9155-8. doi: 10.1021/jo035362e.
The thermal cycloaddition of beta-disulfonyl iodonium ylides to cyclic alkenes affords exclusively 1,2,3-trisubstituted cis(1,2)/cis(2,3)-configured benzocyclopentenes by an electrophilic attack of the ylide on the olefinic double bond. This unsual transformation provides a convenient and direct method for the diastereoselective synthesis of functionalized bicyclo[3.3.0]octanes (characteristic structural units contained in polyquinane natural products), when cyclopentenes are used as cycloalkene partner.
β-二磺酰碘鎓叶立德与环状烯烃的热环加成反应通过叶立德对烯烃双键的亲电进攻，专一性地生成1,2,3-三取代的顺式(1,2)/顺式(2,3)构型的苯并环戊烯。当环戊烯用作环烯烃反应物时，这种不同寻常的转化为功能化双环[3.3.0]辛烷（聚环烷天然产物中包含的特征结构单元）的非对映选择性合成提供了一种简便直接的方法。
