Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences
Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences
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DOI：
10.1021/jo0525027
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发表时间：
2006-03-17
影响因子：
3.6
通讯作者：
Rodríguez-Acebes, R
中科院分区：
文献类型：
--
作者：
Alcaide, B;Almendros, P;Rodríguez-Acebes, R
通过不同的金属离子介导的羰基加成/环化反应顺序，发展了一种新的合成双螺环功能化的螺环羟吲哚的方法。通过稳定的有机铟试剂与靛红在水溶液中的区域选择性加成反应，得到了螺环化前体2-吲哚啉酮基高烯丙醇、（丁二烯-1，3-二烯-2-基）甲醇和α-联烯醇。上述不饱和醇衍生物的钌-、银-和钯-催化的反应提供氧杂螺羟吲哚。
A novel approach to diversely functionalized spirocyclic oxindoles has been developed by using different metal-mediated carbonyl-addition/cyclization reaction sequences. Spirocyclization precursors, 2-indolinonetethered homoallylic alcohols, (buta-1,3-dien-2-yl)methanols, and alpha-allenols have been obtained by regioselective addition of stabilized organoindium reagents to isatins in aqueous environment. Ruthenium-, silver-, and palladium-catalyzed reactions of the above unsaturated alcohol derivatives provided oxaspiro oxindoles.