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.

引用

页码：3355 / 3361

页数：7

共 27 条

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