A large-scale synthesis of enantiomerically pure γ-hydroxy-organochalcogenides

Enantiomerically pure (R)- and (S)-γ-hydroxy-organochalcogenides are prepared using poly-[R]-3-hydroxybutanoate (PHB) as the starting material.

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(R)-1-(nButylthio)-3-butanolC8H18OS99.9% ee[α]D24=-8.5 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-1-(nButylsellanyl)-3-butanolC8H18OSe99.9% ee[α]D23=-6.2 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-1-(nButyltellanyl)-3-butanolC8H18OTe99.9% ee[α]D25=-7.9 (c 1.0, CH2Cl2)Absolute configuration: (R)

(R)-1-(Phenylthio)-3-butanolC10H14OS99.9% ee[α]D24=-29.4 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-1-(Phenylsellanyl)-3-butanolC10H14OSe99.9% ee[α]D24=-40.9 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-1-(Phenyltellanyl)-3-butanolC10H14OTe99.9% ee[α]D24=-9.9 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-O-Acetyl-1-(nbutylthio)-3-butanolC2H16O2S99.9% ee[α]D19=+3.5 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-O-Acetyl-1-(nbutylsellanyl)-3-butanolC2H16O2Se99.9% ee[α]D24=+10.1 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-O-Acetyl-1-(nbutyltellanyl)-3-butanolC2H16O2Te99.9% ee[α]D25=+19.5 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-O-Acetyl-1-(phenylthio)-3-butanolC12H16O2S99.9% ee[α]D24=-7.7 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-O-Acetyl-1-(phenysellanyl)-3-butanolC12H16O2Se99.9% ee[α]D26=+5.1 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-O-Acetyl-1-(phenytellanyl)-3-butanolC12H16O2Te99.9% ee[α]D24=+16.6 (c 1.0, CHCl3)Absolute configuration: (R)

(R)-butane-1,3-diolC14H10O299.9% ee[α]D24=-30.0 (c 1.0, EtOH)Absolute configuration: (R)

(R)-3-hydroxybutyl-4-methylbenzenesulfonateC11H16O4S99.9% ee[α]D23=-14.9 (c 1.0, CH2Cl2)Absolute configuration: (R)