433332-20-8Relevant academic research and scientific papers
A direct preparation of silyl oxazoles: A dramatic chemoselectivity difference between R3SiOTf and R3SiCl
Miller, Ross A.,Smith, Randi M.,Karady, Sandor,Reamer, Robert A.
, p. 935 - 938 (2002)
General, highly selective silylation conditions for the ambident oxazole anion (isocyano enolate) have been found. The chemoselectivity between O-silylation and C-silylation changed from 99:1 upon switching from R3SiCl to R3/sub
Oxazole Synthesis by Sequential Asmic-Ester Condensations and Sulfanyl-Lithium Exchange-Trapping
Mueller, Louis G.,Chao, Allen,Alwedi, Embarek,Natrajan, Maanasa,Fleming, Fraser F.
supporting information, p. 1500 - 1503 (2021/03/08)
Oxazoles are rapidly assembled through a sequential deprotonation-condensation of Asmic, anisylsulfanylmethylisocyanide, with esters followed by sulfanyl-lithium exchange-trapping. Deprotonating Asmic affords a metalated isocyanide that efficiently traps esters to afford oxazoles bearing a versatile C-4 anisylsulfanyl substituent. Interchange of the anisylsulfanyl substituent is readily achieved through a first-in-class sulfur-lithium exchange-electrophilic trapping sequence whose versatility is illustrated in the three-step synthesis of the bioactive natural product streptochlorin.
