1391708-69-2Relevant academic research and scientific papers
Sequential Au/Cu Catalysis: A Two Catalyst One-Pot Protocol for the Enantioselective Synthesis of Oxazole α-Hydroxy Esters via Intramolecular Cyclization/Intermolecular Alder-Ene Reaction
Nalivela, Kumara Swamy,Rudolph, Matthias,Baeissa, Elham S.,Alhogbi, Basma G.,Mkhalid, Ibraheem A. I.,Hashmi, A. Stephen K.
, p. 2183 - 2190 (2018/04/30)
A convenient protocol for the enantioselective synthesis of oxazole α-hydroxy ester derivatives 4 from readily available propargylamides 1 and alkylglyoxylates 3 was developed. The first step of the one-pot procedure is the selective intramolecular in situ formation of an alkylideneoxazoline 2, which then in an intermolecular reaction is enantioselectively transformed to the oxazole α-hydroxy ester derivatives 4 in quantitative yield and good to excellent enantioselectivity via an asymmetric copper(II)-catalyzed Alder-ene reaction. (Figure presented.).
From propargylic amides to functionalized oxazoles: Domino gold catalysis/oxidation by dioxygen
Hashmi, A. Stephen K.,Blanco Jaimes, Maria Camila,Schuster, Andreas M.,Rominger, Frank
, p. 6394 - 6408 (2012/09/22)
A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroperoxides bearing the heteroaromatic oxazoles. Experiments addressing the reaction mechanism reveal a radical pathway for this autoxidation process. The hydroperoxides could conveniently be converted to the corresponding alcohols by reduction with sodium borohydride.
