NHC-Catalyzed Three-Component Domino Reaction of Bromoenals with Oxindoles: Diastereoselective Assembly of Spirooxindole 4H-Pran-2-Ones
作者单位：School of Chemistry and Materials Science Jiangsu Normal University
会议名称：《中国化学会第十四届全国有机合成化学学术研讨会》
会议日期：2017年
学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学]
关 键 词：spirooxindoles N-heterocyclic carbenes α,β-unsaturated acyl azloliums
摘 要：Spirooxindoles are frequently present as important cores in large amounts of natural products,pharmaceutically relevant synthetic compounds with highly biological activities. As a novel class of spirooxindoles, only a few investigations have been focused on the syntheses and bioactivities of spirooxindole 4H-pyran-2-ones. N-heterocyclic carbene(NHC)catalysis has been used as a powerful tool for a large number of untypical chemical transformations. Among these conversions,α,β-unsaturated acyl azoliums have emerged as fascinating1,3-biselectrophile synthons with unique and unprecedented chemistry that were pioneered by Zeitler in 2006. The well-explored reactions involved NHC-mediated formal[3+3]annulations ofα,β-unsaturated acyl azoliums with various 1,3-bisnucleophiles to afford functionalized dihydropyranones and dihydropyridinones. However,to the best of our knowledge,the three-component domino reaction of bromoenals are rarely *** continuation of our studies on the exploration of NHC-catalyzed annulations for the synthesis of diverse heterocyclic systems, we shall herein report that oxindoles serve as 1,1-bisnucleophiles to undergo three-component domino reaction,which provides a new access to spirooxindole 4H-pyran-2-ones.