Dihydropyranone formation by ipso C-H activation in a glucal 3-carbamate-derived rhodium acyl nitrenoid.

Dihydropyranone formation by ipso C-H activation in a glucal 3-carbamate-derived rhodium acyl nitrenoid.
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在葡萄糖 3-氨基甲酸酯衍生的铑酰基氮烯化合物中通过 ipso C-H 活化形成二氢吡喃酮。

DOI:
10.1021/jo101599q
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发表时间:
2011
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Rojas,ChristianM
Rojas,ChristianM
中科院分区:
--
文献类型:
--
作者:
Hurlocker,Brisa;Abascal,NadiaC;Repka,LindsayM;Santizo-Deleon,Elsy;Smenton,AbigailL;Baranov,Victoria;Gupta,Ritu;Bernard,SarahE;Chowdhury,Shenjuti;Rojas,ChristianM

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通过使用(N-甲苯磺酰氧基)-3-O-氨基甲酰基-d-葡萄糖醛10,这消除了对高价碘(III)氧化剂的需要,我们提供了铑nitrenoid介导的dipsoC −H活化作为C3-氧化二氢吡喃酮产物来源的证据3。该系统可能特别容易受到这种途径的影响,因为在氢化物转移到铑络合的酰基氮烯时容易形成阳离子。
By using (N-tosyloxy)-3-O-carbamoyl-d-glucal10, which removes the need for a hypervalent iodine(III) oxidant, we provide evidence for rhodium nitrenoid-mediatedipsoC−H activation as the origin of a C3-oxidized dihydropyranone product3. This system may be especially susceptible to such a pathway because of the ease of forming a cation upon hydride transfer to the rhodium-complexed acyl nitrene.
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DOI: --
发表时间: 2011
期刊:
影响因子: --
作者:
S. A. Moteki;S. Shirakawa;and K. Maruoka
通讯作者: and K. Maruoka