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Stereoselective Construction of Spiro‐Indolenine Frameworks through a Prins/Friedel–Crafts Cyclization Cascade Reaction
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2018-04-16 , DOI: 10.1002/ejoc.201701812
Rapelli Chandrashekhar 1 , Sahithya Phani Babu Vemulapalli 2 , Balasubramanian Sridhar 3 , Basireddy Venkata Subba Reddy 1
Affiliation  

A strategy has been developed for the synthesis of pharmaceutically relevant spiroindolenines in a single step that proceeds through a sequential Prins/Friedel–Crafts cyclization. A 3‐({[2‐(1H‐indol‐3‐yl)ethyl]amino}methyl)but‐3‐en‐1‐ol derivative and various aldehydes react under mild conditions, leading to the products in good yields with high diastereoselectivity (Ns: 2‐nitrobenzenesulfonyl, TFA: trifluoroacetic acid, DCM: dichloromethane).
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中文翻译:

通过Prins / Friedel-Crafts环化级联反应立体构筑螺-吲哚骨架。

已经开发了一种策略,可通过一步的Prins / Friedel-Crafts环化过程一步合成合成药物相关的螺环吲哚胺。3-({[[(2-(1 H-吲哚-3-基)乙基]氨基}甲基)丁-3-烯-1-醇衍生物与各种醛在温和的条件下反应,导致产物收率高高非对映选择性(Ns:2-硝基苯磺酰基,TFA:三氟乙酸,DCM:二氯甲烷)。
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更新日期:2018-04-16
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