Tetrapropylammonium perruthenate, preparation

Most compounds of this type are derived from methyl hexosides methyl 2,6 3,4-dianhydro-a-D-altropyranoside309 398 400 516 and methyl 2,5 3,6-dianhydro-a- and /J-n-mannol iiranosides.517 From hexuloses, the synthetically useful l,5 3,6-dianhydro-D-<2raZ)i o-hex-2-ulose (172) has been prepared by regioselective monobenzylation of l,5 3,6-dianhydro-D-mannitol at C-4 (171a — 171b) followed by oxidation with tetrapropylammonium perruthenate.518... 

Griffith, W. P., Ley, S. V., Whitcombe, G. P., White, A. D. Preparation and use of tetrabutylammonium perruthenate (TBAP reagent) and tetrapropylammonium perruthenate (TPAP reagent) as new catalytic oxidants for alcohols. J. Chem. Soc., Chem. Common. 1987,1625-1627. 

As a further extension, the Kim group very recently developed the aerobic oxidation and [l,5]-hydride transfer/cyclization sequence starting from readily available ortho tertiary amine substituted cinnamyl alcohols 24 (Scheme 4.12). The tetrapropylammonium perruthenate (TPAP) was identified as the competent catalyst for the initial aerobic oxidation of the allylic alcohols. The synthetically useful tetrahydroquinoline derivatives 25 were prepared in moderate yields and high level of enantioselectivity. 

Solandelactones A, B, E, and F have been synthesized by White et al., in which the diene side chain was installed using a Nozaki-Hiyama-Kishi reaction. Aldehydes 48 and 49 were prepared by tetrapropylammonium perruthenate oxidation of the corresponding alcohols and were immediately treated with CrCla and NiCl2 to afford the natural products solandelactone A, B, E, and F (Scheme 12.36). ... 

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