Hydroxymethylphosphine oxides

Kielbasinski P, Albiycht M, Luczak J, Mikolajczyk M (2002) Enzymatic reactions in ionic liquids lipase-catalysed kinetic resolution of racemic, P-chiral hydroxymethanephosphinates and hydroxymethylphosphine oxides. Tetrahedron Asymm 13 735-738... 

Hydroxymethylphosphine oxides (149) proved to be excellent substrates for kinetic resolution, as reported by Shioji and co-workers (Scheme 6.58). ° ... 

Lipase-catalysed enantioselective acylation of hydroxymethylphosphine oxides. 

Vinylic phosphate (192) has been reported to react as Michael acceptor with alcohols in basic catalytic conditions to afford, in the case of ethylene glycol, the expected adduct (193). Under similar conditions, the hydroxymethylphosphine oxide (194), used as alcoholic reagent, loses formaldehyde and the salt (195) thus generated adds to vinylphosphine oxide (192) in a Michael fashion to produce 1,2-diphosphosphine oxide (196). 4... 

Calix[n]arenes (n = 4, 6) existing in the cone, 1,3-alternate or 1,3,5-alternate conformations and functionalized by two, four or six Bu2P(0)CH20 groups were synthesized by the alkylation of hydroxy-calix[4,6]arenes with the tosylate of dibutyl-hydroxymethylphosphine oxide (Schemes 27-1, 27-2 and 28). In the preparation of another calixarene, the benzyl chloride moieties alkylated the hydroxy groups of four dibutyl-hydroxymethylphosphine oxide molecules (Scheme 29). Due to the calixarene effect , the phosphine oxides are potential extractants for Ru/Zn complexes. 

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