Synthesis of Spiro[piperidine-3,3′-oxindoles] via Gold(I)-Catalyzed Dearomatization of N-Propargyl- and N-Homoallenyl-2-bromotryptamines

被引：41
|
作者：
Magne, Valentin [1 ]
Blanchard, Florent [1 ]
Marinetti, Angela [1 ]
Voituriez, Arnaud [1 ]
Guinchard, Xavier [1 ]
机构：
[1] Univ Paris Saclay, Univ Paris Sud, CNRS UPR 2301, Inst Chim Subst Nat, 1 Ave Terrasse, F-91198 Gif Sur Yvette, France
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 21期
关键词：
alkynes; allenes; gold catalysis; homogeneous catalysis; indoles; spiro compounds; ONE-POT SYNTHESIS; GOLD CATALYSIS; CASCADE REACTIONS; NATURAL-PRODUCTS; INDOLES; ALKYNES; HYDROARYLATION; CARBAZOLES; STRATEGIES; OXINDOLES;
D O I：
10.1002/adsc.201600398
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
N-Propargyl- and N-homoallenyl-2-bromo-beta-tryptamines undergo gold(I)-catalyzed dearomatizing cyclizations to afford 2-bromospiroindolenines that are in situ hydrolyzed to furnish spirooxindoles in a one-pot process. Tryptophane derivatives (R-2 = CO2Et) led upon cyclization to chiral spirooxindoles in excellent diastereoselectivities.
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收藏
页码：3355 / 3361
页数：7
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