Enantioselective Alkylation of 2-Oxindoles Catalyzed by a Bifunctional Phase-Transfer Catalyst: Synthesis of (-)-DebromoflustramineB

被引：23

作者：

Craig, Ryan ^{[1
]}

Sorrentino, Emiliano ^{[1
]}

Connon, Stephen J. ^{[1
]}

机构：

[1] Univ Dublin, Trinity Coll, Synth & Solid State Pharmaceut Ctr, Trinity Biomed Sci Inst,Sch Chem, Dublin 2, Ireland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 18期

基金：

爱尔兰科学基金会;

关键词：

alkylation; enolates; oxindoles; phase-transfer catalysis; pyrroloindoline; BRYOZOAN FLUSTRA-FOLIACEA; ORGANOCATALYTIC CONSTRUCTION; 3-SUBSTITUTED OXINDOLES; PYRROLOINDOLINES; SPIROOXINDOLES; STEREOCENTERS; STRATEGIES; ALKALOIDS; BEARING; ESTERS;

D O I：

10.1002/chem.201800313

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new bifunctional phase-transfer catalyst that employs hydrogen bonding as a control element was developed to promote efficient enantioselective S(N)2 reactions for the construction all-carbon quaternary stereocenters in high yield and excellent enantioselectivity (up to 97%ee) utilizing the alkylation of a malleable oxindole substrate. The utility of the methodology was demonstrated through a concise and highly enantioselective synthesis of (-)-debromoflustramineB.

引用

页码：4528 / 4531

页数：4

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