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(S)-2-Methyl-CBS-oxazaborolidine monohydrate_Molecular_structure_CAS_112022-81-8)
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(S)-2-Methyl-CBS-oxazaborolidine monohydrate

Catalog No. L09219 Name Alfa Aesar
CAS Number 112022-81-8 Website
M. F. C18H20BNO Telephone
M. W. 277.1685 Fax
Purity 94% Email
Storage Chembase ID: 141220

SYNONYMS

Title
(S)-2-甲基-CBS-氧杂硼啶单水合物
IUPAC name
(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
IUPAC Traditional name
(3aS)-1-methyl-3,3-diphenyl-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole
Synonyms
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole

DATABASE IDS

CAS Number 112022-81-8
Beilstein Number 8492123
MDL Number MFCD00078439

PROPERTIES

Purity 94%
Melting Point 115-121°C
Optical Rotation -67 (c=1 in methanol)
TSCA Listed

DETAILS

REFERENCES

  • Air-stable solid prepared by a modification of Corey's procedure, on which his literature results were based. For anhydrous reagent, see (S)-2-Methyl-CBS-oxazaborolidine, L14583.
  • Catalyst for the CBS (Corey, Bakshi, Shibata) reduction of prochiral ketones with borane-THF, with high enantioselectivity (see (S)-(-)-ɑ,ɑ-Diphenylprolinol, L09217): J. Am . Chem. Soc., 109, 7925 (1987):
  • For successful use of this system in a scaled up asymmetric synthesis of the antiarrythmia agent d-Sotalol, see: Org. Process Res. Dev., 1. 176 (1997). For use in enantioselective reduction of ketones containing heteroatoms, see: Tetrahedron Lett., 34, 785 (1993). For the asymmetric reduction of ɑ-ketoimines, see: Tetrahedron Lett., 35, 5551 (1994).
  • 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).