CAN ceric ammonium

CAN.ceric ammonium nitrate (ammonium cerium(IV) nitrate)... 

Release and Reactivity of tf-o-QMs Although the r 2-o-QM Os complexes 11 are stable when exposed to air or dissolved in water, the quinone methide moiety can be released upon oxidation (Scheme 3.8).16 For example, reaction of the Os-based o-QM 12 with 1.5 equivalents of CAN (ceric ammonium nitrate) in the presence of an excess of 3,4-dihydropyran led to elimination of free o-QM and its immediate trapping as the Diels-Alder product tetrahydropyranochromene, 14. Notably, in the absence of the oxidizing agent, complex 12 is completely unreactive with both electron-rich (dihydropyran) and electron-deficient (A-methylmaleimide) dienes. 

CAN Ceric ammonium nitrate CDI N,N -Carbonyldiimidazole DCC N,N -Dicyclohexylcarbodiimide DIC N,N -Diisopropylcarbodiimide DMAP 4-(Dimethylamino)pyridine DMF N,N-Dimethylformamide DMSO Dimethyl sulfoxide... 

SCHEME 12.20 Total synthesis of starfish ganglioside LLG-3. CAN, ceric ammonium nitrate, DTBMP, 2,6-di-tcrt-butyl-4-methylpyridine, HOBt, 1-hydroxybenzotriazole. 

SCHEME 13.1 Synthesis of the pseudopentasaccharide intermediate 9. CAN, ceric ammonium nitrate PMB, p-methoxybenzyl Pyr, pyridine TBAF, tetrabutylammonium fluoride Tf, triflyl. 

Ac, acetyl AIBN, azobis(isobutanonitrile) All, allyl AR, aryl Bn, benzyl f-BOC, ferf-butoxycarbonyl Bu, Butyl Bz, benzoyl CAN, ceric ammonium nitrate Cbz, benzyloxycarbonyl m-CPBA, m-chloroperoxybenzoic acid DAST, diethylaminosulfur trifluoride DBU, l,8-diazabicyclo[5.4.0]undec-7-ene DCC, /V. /V - d i eye I oh e x y I c ar bo -diimide DCM, dichloromethyl DCMME, dichloromethyl methyl ether DDQ, 2,3-dichloro-5,6-dicyano-l,4-benzoquinone DEAD, diethyl azodicarboxylate l-(+)-DET, L-(+)-diethyl tartrate l-DIPT, L-diisopropyl tartrate d-DIPT, D-diisopropyl tartrate DMAP, 4-dimethylaminopyridine DME, 1,2-dimethoxyethane DMF, /V./V-dimethylformamide DMP, 2,2-dimethoxypropane Et, ethyl Im, imidazole KHMDS, potassium hexamethyldisilazane Me, methyl Me2SO, dimethyl sulfoxide MOM, methoxymethyl MOMC1, methoxymethyl chloride Ms, methylsulfonyl MS, molecular sieves NBS, N-bromosuccinimide NIS, /V-iodosuccinimide NMO, /V-methylmorpho-line N-oxide PCC, pyridinium chlorochromate Ph, phenyl PMB, / -methoxvbenzyl PPTs, pyridiniump-toluenesulfonate i-Pr, isopropyl Py, pyridine rt, room temperature TBAF, tetrabutylammonium fluoride TBS, ferf-butyl dimethylsilyl TBDMSC1, f-butylchlorodimethylsilane Tf, trifhioromethylsulfonyl Tf20, trifluoromethylsulfonic anhydride TFA, trifluoroacetic acid THF, tetrahydrofuran TMS, trimethylsilyl TPAP, tetra-n-propylammonium perruthenate / -TsOH. / -toluenesulfonic acid... 

Scheme 42. Use of the Dotz reaction (CAN = ceric ammonium nitrate) in the synthesis of benzo[a]anthraquinone 167 [112]...

The tandem aldol reaction simply involves adding an aldehyde to the lithium enolate before work-up. Since it is a Z-enolate we can expect a syn aldol. The Z -enolate 90 is indeed formed (we are drawing the molecules in a different way to make the aldol stereochemistry clearer) and it does give a syn-aldol with the added advantage that only one of the two possible. vyn-aldols 90 predominates. The two benzylic groups can be removed, the first with CAN , ceric ammonium nitrate, Ce(IV)(NH4)2(N03)6 and the second by reduction, to give one enantiomer of 95. 

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