Synthesis of acetyldimethyl(phenyl)silane and its enantioselective conversion into (R)-(1-hydroxyethyl)dimethyl(phenyl)silane by plant cell suspension cultures of Symphytum officinale L. and Ruta graveolens L.

Article abstract of DOI:10.1016/0022-328X(93)80452-H

Starting from chlorodimethyl(phenyl)silane (3), acetyldimethyl(phenyl)silane (1) was prepared by a two-step synthesis in a total yield of 90percent PhMe2SiC(OMe)=CH2 (4) <*> PhMe2SiC(O)Me (1)>.The prochiral acetylsilane 1 was transformed enantioselectively into (R)-(1-hydroxyethyl)dimethyl(phenyl)silane <(R)-2> using plant cell suspension cultures of Symphytum officinale L. or Ruta graveolens L.Under preparative conditions (300-mg scale, not optimized), (R)-2 was isolated in 15percent (Symphytum) and 9percent yield (Ruta), respectively.The enantiomeric purities of the products were 81percent ee (Symphytum) and 60percent ee (Ruta), respectively.