(S)-2-Methyl-CBS-oxazaborolidine monohydrate

• Catalog No.: L09219
• CAS Number: 112022-81-8
• M. F.: C18H20BNO
• M. W.: 277.1685
• Purity: 94%

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: 否

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).