D. A. Evans, N. Finney Hydrazone Transformations-5 Chem 206 Alkene Walk: Syntheses Sulfonylhydrazone Reductions: Alcohol Deoxygenation Eto2 CN=NCO2Et RCH2-OH Me 1. NH2NHTS, THF, 25C Ph30℃0RC4 3. NaOAC3H20 RCH2-N=N-H Mitsunobo Reaction) -HSO2Ts Compactin Wendler N. L. et al. Tet. Lett. 1982. 23. 5501 Meo MeO The stereochemical course of the hydrazone reduction may be The intervention of radicals has been implicated (again) stereospecifically transferred via the 1, 3-rearrangement DAEL 1. NH NHTS, THF, 25"C( 2 CB 3. NaOAC3H20 Maryanoff, B E, et al. Tet. Lett. 1992, 33, 5009. 10 cases reported: A Myers, et al. JACS 1997, 119, 8572O H H MeO AcO Me O CO2Et N H H MeO AcO Me H N Ts H –HSO2Ts –OAc [H] AcO MeO H H Me H CO2Et H N H H MeO AcO Me N H RCH2 OH NO2 SO2–NHNH2 OH OH OMe MeO Bu OH Me N O OH EtO2CN NCO2Et Ph3P, –30 °C ● RCH2 H RCH2 N S O O Ar NH2 Bu H Me N O Me OMe MeO RCH2 RCH2 N N–H In● ● Me S O O– Ar Hydrazone Transformations-5 Chem 206 Sulfonylhydrazone Reductions: Alcohol Deoxygenation ~0 °C 80% 86% 86% The intervention of radicals has been implicated (again): 10 cases reported: A. Myers, et al. JACS 1997, 119, 8572. D. A. Evans, N. Finney Compactin, Wendler, N. L., et al. Tet. Lett. 1982, 23, 5501. 1. NH2NHTs, THF, 25°C Alkene Walk: Syntheses 1. NH2NHTs, THF, 25°C 2. CB 3. NaOAc•3H2O (60%) Topiramate, Maryanoff, B. E., et al. Tet. Lett. 1992, 33, 5009. The stereochemical course of the hydrazone reduction may be stereospecifically transferred via the 1, 3-rearrangement (Mitsunobo Reaction) Org Rxns Volume 29 2. Catecholborane 3. NaOAc•3H2O