Enzymatic kinetic resolution of α-hydroxysilanes

The enzymatic kinetic resolution of α-hydroxysilanes where the silicon bears a variety of substituents has been explored. Reactions were performed on various α-hydroxysilanes with several commercially available enzymes, solvents, acetylation reagents, and temperatures. The resulting optically active α-hydroxysilanes and their corresponding acetates were obtained in varying yields and ees.

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(R)-1-HydroxyallyltrimethylsilaneC6H14OSiEe = 73%[α]D20=-7.1 (c 1.05, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (1R)

(S)-Acetic acid 1-(trimethylsilyl)-allyl esterC8H16O2SiEe = 98%[α]D20=-17.5 (c 1.03, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (1S)

(R)-1-(Dimethylphenysilyl)-2-propen-1-olC11H16OSiEe = 99%[α]D20=-8.8 (c 1.04, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (1R)

(S)-1-HydroxyallyltrimethylsilaneC6H14OSiEe = 89%[α]D20=+8.3 (c 1.21, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (1S)

(S)-Acetic acid 1-(dimethylphenylsilyl)-prop-2-enyl esterC13H18O2SiEe = 99%[α]D20=-10.1 (c 1.26, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (1S)

(S)-1-(Dimethylphenysilyl)-2-propen-1-olC11H16OSiEe = 93%[α]D20=+8.2 (c 1.12, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (1S)