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L09217 (S)-(-)-alpha,alpha-Diphenylprolinol, 98%

CAS Number

Stock No. Size Price ($) Quantity Availability
L09217-03 1g 72.00
L09217-06 5g 228.00
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(S)-(-)-alpha,alpha-Diphenylprolinol, 98%


Chemical Properties

Formula Weight
Melting point
Storage & Sensitivity
Ambient temperatures.
Soluble in chloroform.


(S)-(-)-alpha,alpha-Diphenylprolinol is used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.


Incompatible with strong oxidizing agents. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

Literature References

Precursor of Corey, Bakshi and Shibata's oxazaborolidine derivatives (CBS catalysts) for enantioselective reduction of prochiral ketones: J. Am. Chem. Soc., 109, 5551 (1987). Ketones are not reduced rapidly by either borane-THF or the oxazaborolidine alone but together they form a complex which reduces ketones rapidly and stereoselectively, permitting reduction with very high ee in the presence of a catalytic amount of the oxazaborolidine: J. Am. Chem. Soc., 109, 7925 (1987).

For use in conjunction with borane generated in situ using NaBH4 and iodine, see: Tetrahedron, 50, 6411 (1994). For an optimized in situ procedure for generation and use of the oxazaborolidine from BMS, see: Tetrahedron: Asymmetry, 7, 3147 (1996). In a comparison with other oxazaborolidine precursors, diphenylprolinol gave the best results (same ref.). For in situ generation of an asymmetric reduction system using trimethyl borate and BMS, see: Synlett, 273 (1997). For the generation and use of the phenyl oxazaborolidine, using Benzeneboronic acid, A14257, see: Tetrahedron Lett., 31, 7415 (1990); 32, 7175 (1991); J. Org. Chem., 57, 7115 (1992). For a detailed comparative study of various alkyl- and aryl-substituted borolidines, see: J. Org. Chem., 56, 763 (1991). For a process for the in situ formation of butyl oxazaborolidines using 1-Butyl­boronic acid, A13725, see: Tetrahedron Lett., 33, 4141 (1992). For use for the catalytic enantioselective synthesis of chiral monosubstituted oxiranes, see: Tetrahedron Lett., 34, 5227 (1993).

For reviews of oxazaborolidines as enantioselective catalysts, see: Angew. Chem. Int. Ed., 31, 729 (1992); 37, 1986 (1998); Tetrahedron: Asymmetry, 3, 1475 (1992). For reviews of the asymmetric reduction of ketones, see: Synthesis, 605 (1992); Chem. Ind. (London), 552 (1994).

See also the preformed catalyst (S)-2-Methyl-CBS-oxazaborolidine, L14583, and (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

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