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Download Organic Syntheses : Volume 53. by A. Brossi PDF

By A. Brossi

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67 eq), CuClO4 (8 mol%) R + E E 51 52 (Eq. 91) E = N(CO2Et)NHCO2Et O NHTs (Eq. 5 h (53%) Ketone silyl enol ethers react with derivatives of diacyl azo compounds at room temperature245 or on heating242,243 (see also Eq. 82) as well as enantioselectively under the influence of silver trifluoromethanesulfonate and BINAP (Eq. 93)244 or copper bis(oxazoline) complexes (Eq. 94). 252 Ketones themselves react with azodicarboxylic esters either thermally246,389,390 or in the presence of potassium carbonate390 but yields are low.

576 Oxidation of intermediates 81 leads to nitrones,577 and reduction to amino alcohol derivatives (Eq. 579,580 NO ClMg 1. THF, –20°, 1 h + Me2N CO2Et 2. FeCl2, NaBH4, rt, 2 h H N (72%) Me2N CO2Et (Eq. 180) CF3 O O Et3N, Et2O + CF3NO N OH (Eq. 181) (65%) –10° O O O Et3N, CHCl3 rt, 1 d N Ph Ph (100%) Ph TMSO O PhNO, CHCl3 rt, 4-6 h Ph OTMS N Ph O 1. HCl, THF, rt 2. Ag2O, C6H6, rt O N Ph 81 (80%) Ph (80%) OH LiAlH4, Et2O, rt or Pd/C, H2, THF, rt Ph H N Ph (75-78%) (Eq. 182) α-Chloronitroso compounds581 react with alkyl- and arylmagnesium reagents582,583 and with trialkylaluminum reagents584 to give nitrones.

32),343 the chloramine-T/osmium tetroxide system (Eq. 99),342 and bis[N -(p-toluenesulfonyl)]selenodiimide (Eq. 345 Nitridomanganese complexes (cf. Eq. 5 h (67%) (Eq. 96) 38 ORGANIC REACTIONS O O OTBS O O NaN3, Ce(NH4)2(NO3)6 O O N3 O MeCN, –15°, 2 h; to rt (70%) (Eq. 97) H OTMS 1. 100°, 15 h + EtO2CN3 OTMS + TsN(Cl)Na (Eq. 98) NHCO2Et (40%) 2. 004 eq), t-BuOH/H2O (1:1) NHTs (Eq. 99) rt, 15 min a t-Bu O t-Bu see List of Abbreviations (34%) 76% ee OSi(Pr-i)3 OSi(Pr-i)3 CH2Cl2, 0° TsNH + "TsN=Se=NTs" (Eq.

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