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Ethynyl‐1,2‐benziodoxol‐3(1 H )‐one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters
Author(s) -
Fernández González Davinia,
Brand Jonathan P.,
Waser Jérôme
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001539
Subject(s) - reagent , silylation , nitro , chemistry , alkyne , acetylene , medicinal chemistry , quaternary carbon , combinatorial chemistry , organic chemistry , catalysis , enantioselective synthesis , alkyl
Hot alkyne! The in situ generation of ethynyl‐1,2‐benziodoxol‐3(1 H )‐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.