期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 1, 页码 152-161出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo902256r
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资金
- EPSRC
- GlaxoSmithKline
- EPSRC [EP/E018750/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/E018750/1] Funding Source: researchfish
Dirhodium tetraacetate catalyzed reaction of alpha-diazo-beta-keto-carboxylates and -phosphonates with arenecarboxamides gives 2-aryloxazole-4-carboxylates and 4-phosphonates by carbene N-H insertion and cyclodehydration. In stark contrast, dirhodium tetrakis(heptafluorobutyrimide) catalysis results in a dramatic change of regioselectivity to give oxazole-5-carboxylates and 5-phosphonates. alpha-Diazo-beta-ketosulfones behave similarly and give 5-sulfonyloxazoles upon dirhodium tetrakis-(heptafluorobutyrarnide) catalyzed reaction with carboxamides. The analogous reactions of thiocarboxamides give the corresponding thiazole-5-carboxylates, -phosphonates, and -sulfones.
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