Ethynyl-1,2-benziodoxol-3(1H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters

被引：165

作者：

Gonzalez, Davinia Fernandez ^{[1
]}

Brand, Jonathan P. ^{[1
]}

Waser, Jerome ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, EPFL SB ISIC LCSO, CH-1015 Lausanne, Switzerland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 31期

基金：

瑞士国家科学基金会;

关键词：

alkynylation; hypervalent compounds; iodine; quaternary carbon atoms; umpolung; ALPHA-AMINO-ACIDS; HYPERVALENT IODINE; ELECTROPHILIC TRIFLUOROMETHYLATION; ALKYNYLIODONIUM SALTS; ASYMMETRIC-SYNTHESIS; SONOGASHIRA REACTION; TERMINAL ACETYLENES; DIRECT ALKYNYLATION; REDUCTIVE CLEAVAGE; MICHAEL ACCEPTORS;

D O I：

10.1002/chem.201001539

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hot alkyne! The in situ generation of ethynyl-1,2-benziodoxol-3(1H)-one (EBX) from a silyl-protected reagent by using TBAF is reported. EBX displayed exceptional acetylene transfer ability onto stabilized enolates (see scheme), even at -78 □°C. The mild reaction conditions allowed the first ethynylation reactions of linear keto, cyano, and nitro esters in high yields to give all-carbon quaternary centers or non-natural amino acids after selective reduction of the nitro group. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9457 / 9461

页数：5

共 63 条

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