| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349384 | Tetrahedron: Asymmetry | 2006 | 4 Pages |
An oxazaborolidine catalyst is readily prepared in situ at 25 °C in THF using (S)-α,α-diphenylpyrrolidinemethanol and borane generated from tetrabutylammonium borohydride/CH3I reagent system. The oxazaborolidine/BH3 reagent system prepared in this way is useful for the reduction of prochiral ketones to the corresponding alcohols with up to 99% ee.
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(R)-1-PhenylethanolC8H10OEe >99%[α]D25=+45 (c 1, MeOH)Source of chirality: asymmetric reductionAbsolute configuration: (R)
(R)-1-(4-Nitrophenyl)ethanolC8H9NO3Ee >96%[α]D25=+30 (c 1, MeOH)Source of chirality: asymmetric reductionAbsolute configuration: (R)
(R)-1-(4-Methylphenyl)ethanolC9H12OEe >95%[α]D25=+40 (c 1.0, MeOH)Source of chirality: asymmetric reductionAbsolute configuration: (R)
(2R)-1,1,2-Triphenyl-1,2-ethanadiolC20H18O2Ee >40%[α]D25=+91 (c 1.0, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (R)
(S)-2-Chloro-1-phenylethanolC8H9ClOEe >82%[α]D25=+39 (c 1.20, cyclohexane)Source of chirality: asymmetric reductionAbsolute configuration: (S)
(S)-2-Bromo-1-phenylethanolC8H9BrOEe >76%[α]D25=+28 (c 1.0, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (S)
(R)-1-Phenylbutan-1-olC10H14OEe >94%[α]D25=+42 (c 0.60, benzene)Source of chirality: asymmetric reductionAbsolute configuration: (R)
(R)-1-Phenylpropan-1-olC9H12OEe >91%[α]D25=+43 (c 1.30, CHCl3)Source of chirality: asymmetric reductionAbsolute configuration: (R)
