Department of Chemistry, Indiana University, Bloomington, Indiana 47405-7102, USA.
Org Lett. 2010 Feb 19;12(4):808-11. doi: 10.1021/ol902833p.
Deprotonation of 2-(phenylsulfonyl)-1,3-oxazole (1) readily provides a useful C-5 carbanion that is reactive with a variety of electrophiles. Aldehydes and ketones are useful substrates, and the formation of 5-iodo- and 5-tri-n-butylstannyl oxazoles affords access to cross-coupling reactions. Subsequent nucleophilic displacement of the 2-phenylsulfonyl group provides a general route for the synthesis of 2,5-disubstituted-1,3-oxazoles.
2-(苯磺酰基)-1,3-噁唑（1）容易脱质子，生成一种有用的 C-5 碳负离子，它可与各种亲电试剂反应。醛和酮是有用的底物，而 5-碘代和 5-三丁基锡基噁唑的形成则可用于交叉偶联反应。随后，2-苯磺酰基的亲核取代为合成 2,5-二取代-1,3-噁唑提供了一种通用途径。
