A new enzymatic approach to (R)-Tamsulosin hydrochloride

An enantioselective baker’s yeast mediated approach to the pharmacologically active (R)-enantiomer of Tamsulosin hydrochloride is reported.

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(1R,2S)-1-(4-Methoxyphenyl)propane-1,2-diolC10H14O3Ee >99%[α]D24=-26.7 (c 1.0, CHCl3)Source of chirality: baker’s yeast-mediated reactionAbsolute configuration: (1R,2S)

(S)-1-(4-Methoxyphenyl)propan-2-olC10H14O2Ee >99%[α]D24=+32.6 (c 1.0, CHCl3)Source of chirality: baker’s yeast-mediated reactionAbsolute configuration: (S)

(S)-1-(4-Methoxyphenyl)propan-2-yl acetateC12H16O3Ee >99%[α]D24=+7.5 (c 1.1, CHCl3)Source of chirality: baker’s yeast-mediated reactionAbsolute configuration: (S)

(S)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl acetateC12H17NO5SEe >99%[α]D24=+7.6 (c 0.99, CHCl3)Source of chirality: baker’s yeast-mediated reactionAbsolute configuration: (S)

(S)-5-(2-Hydroxypropyl)-2-methoxybenzenesulfonamideC10H15NO4SEe >99%[α]D24=+24.1 (c 0.95, MeOH)Source of chirality: baker’s yeast-mediated reactionAbsolute configuration: (S)

(R)-5-(2-Azidopropyl)-2-methoxybenzenesulfonamideC10H14N4O3SEe >99%[α]D24=-26.4 (c 0.95, CHCl3)Source of chirality: baker’s yeast-mediated reactionAbsolute configuration: (R)

(R)-5-(2-(2-(2-Ethoxyphenoxy)ethylamino)propyl)-2-methoxybenzenesulfonamide hydrochlorideC20H29ClN2O5SEe >99%[α]D24=-4.1 (c 0.45, MeOH)Source of chirality: baker’s yeast-mediated reactionAbsolute configuration: (R)