2013
DOI: 10.1021/jo400753n
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Direct Synthesis of 2,5-Disubstituted Oxazoles through an Iodine-Catalyzed Decarboxylative Domino Reaction

Abstract: An efficient iodine-catalyzed synthesis of highly substituted oxazoles is presented. Starting from readily available aryl methyl ketones, β-keto esters, or styrenes, in combination with α-amino acids as amine-containing coupling partners, the corresponding 2-alkyl-5-aryl- substituted oxazoles were obtained in up to 80% yield via a decarboxylative domino reaction.

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Cited by 48 publications
(19 citation statements)
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“…Oxone 是商品化的过硫酸氢钾复合盐, 也是有机合 成中经常使用的一类氧化剂. 2013 年 Nachtsheim 小组 [94] 使用 Oxone/I 2 的组合可以完成甲基酮与氨基酸生成多取 代噁唑的反应(Scheme 38). 其中氨基酸的羧基可以在 该体系下脱除, 从而将氨基酸的氮原子引入到噁唑骨架 内.…”
Section: Lewis 酸催化剂unclassified
“…Oxone 是商品化的过硫酸氢钾复合盐, 也是有机合 成中经常使用的一类氧化剂. 2013 年 Nachtsheim 小组 [94] 使用 Oxone/I 2 的组合可以完成甲基酮与氨基酸生成多取 代噁唑的反应(Scheme 38). 其中氨基酸的羧基可以在 该体系下脱除, 从而将氨基酸的氮原子引入到噁唑骨架 内.…”
Section: Lewis 酸催化剂unclassified
“…The reaction is highly sensitive with respect to the solvent used. It proceeds efficiently in DMSO which also points towards the involvement of a Kornblum oxidation at the start of the reaction sequence …”
Section: Decarboxylative Functionalization Of Amino Acids and Their Dmentioning
confidence: 90%
“…An iodine‐catalyzed decarboxylative domino reaction was described by Nachtsheim and co‐workers to synthesize 2‐alkyl‐5‐aryloxazoles 172 from aryl methyl ketones or styrenes 428 and α‐amino acids 164 in the presence of DMSO as solvent (Scheme ) . The reaction was conducted in DMSO which strongly supported an initial Kornblum oxidation pathway.…”
Section: Miscellaneous Reactionsmentioning
confidence: 97%