Wei Yuan, Liu Zunwu, Wu Xinxin, Fei Jie, Gu Xiaodong, Yuan Xiaoqian, Ye Jinxing
Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P. R. China).
Chemistry. 2015 Dec 21;21(52):18921-4. doi: 10.1002/chem.201503530. Epub 2015 Nov 12.
An unprecedented remote construction of chiral vicinal tertiary and quaternary centers by a catalytic asymmetric 1,6-conjugate addition of prochiral carbon nucleophiles to cyclic dienones has been developed. Both 5H-oxazol-4-ones and 2-oxindoles were found to be very efficient carbon nucleophiles in this reaction at a remote position, giving products with excellent enantio- and diastereoselectivities (up to 99% ee and >19:1 d.r. for 5H-oxazol-4-ones and up to 97% ee and >19:1 d.r. for 2-oxindoles).
通过催化不对称的前手性碳亲核试剂对环状二烯酮进行1,6-共轭加成，实现了手性邻位叔碳和季碳中心的前所未有的远程构建。发现5H-恶唑-4-酮和2-氧化吲哚在该反应中作为远程位置的非常有效的碳亲核试剂，得到具有优异对映选择性和非对映选择性的产物（5H-恶唑-4-酮的对映体过量高达99%，非对映体比例>19:1；2-氧化吲哚的对映体过量高达97%，非对映体比例>19:1）。
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