Lipase-catalyzed resolution of β-hydroxy selenides

Eleven β-hydroxy selenides were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30 °C. This approach provided, in several cases, both enantiomers in high enantiomeric excess. The role of the size of substituents and the behaviour of cyclic β-hydroxy selenides is also discussed. Enantiopure β-hydroxy selenides are useful building blocks. As an application of this chemistry, enantiopure (1S,2R)-indene oxide was obtained in one step from the proper enantiopure β-hydroxy selenide.

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(R)-1-Chloro-3-(phenylseleno)-propan-2-yl acetateC11H13ClO2SeEe = 95%[α]D23=-8.8 (c 0.30, CHCl3)Absolute configuration: R

(R,R)-2,3-Dihydro-1-(phenylseleno)-1H-inden-2-yl acetateC17H16O2SeEe = >99%[α]D27=+25.6 (c 1.19, CHCl3)Absolute configuration: R,R

(R,R)-1,2,3,4-Tetrahydro-2-(phenylseleno)naphthalen-1-yl acetateC18H18O2SeEe = 96%[α]D26=-51.2 (c 0.26, CHCl3)Absolute configuration: R,R

(R)-1-(Phenylseleno)-but-3-en-2-yl acetateC12H14O2SeEe = 80%[α]D26=-5.4 (c 0.99, CHCl3)Absolute configuration: R

(R)-1-(Phenylseleno)-pent-4-en-2-yl acetateC13H16O2SeEe = 94%[α]D26=-16.2 (c 0.87, CHCl3)Absolute configuration: R

(S)-1-Chloro-3-(phenylseleno)-propan-2-olC9H11ClOSeEe = 84%[α]D23=+19.25 (c 0.32, CHCl3)Absolute configuration: S

(R)-1-Phenyl-2-(phenylseleno)ethanolC14H14OSeEe = 44%[α]D26=-8.6 (c 0.90, CHCl3)Absolute configuration: R

(S)-1-Phenyl-2-(phenylseleno)ethyl acetateC16H16O2SeEe = 46%[α]D26=+13.2 (c 1.38, CHCl3)Absolute configuration: S

(R,R)-2-(Phenylseleno)-cyclopentyl acetateC13H16O2SeEe = >99%[α]D28=-2.2 (c 1.02, CHCl3)Absolute configuration: R,R

(S)-2-(Phenylseleno)-1-thiophen-2-yl-ethanolC12H12OSSeEe = 58%[α]D25=+4.1 (c 0.73, CHCl3)Absolute configuration: S

(S,S)-2,3-Dihydro-2-(phenylseleno)-1H-inden-1-olC15H14OSeEe = >99%[α]D26=+3.7 (c 0.83, CHCl3)Absolute configuration: S,S

(S)-1-(Phenylseleno)-pent-4-en-2-olC11H14OSeEe = >99%[α]D26=+30.65 (c 0.65, CHCl3)Absolute configuration: S

(S)-1-(Phenylseleno)-hex-5-en-2-olC12H16OSeEe = 85%[α]D24=+36.3 (c 0.83, CHCl3)Absolute configuration: S