(R)-2-Methyl-CBS-oxazaborolidine

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(R)-2-Methyl-CBS-oxazaborolidine[1]
File:(R)-2-Methyl-CBS-oxazaborolidine.jpg
IUPAC name
(3aR)-1-Methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole 
Other name
(R)-Methyl oxazaborolidine
(R)-(+)-2-methyl-CBS-oxazaborolidine
Identifiers
CAS number:112022-83-0
ChemSpider:8014210
Jmol-3D images:Image 1
SMILES
O2B(N1CCC[C@@H]1C2(c3ccccc3)c4ccccc4)C
InChI
1S/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)
16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m1/s1
Properties
 Molecular formula:C18H20BNO
Molar mass:277.17
Appearance:Colorless to pale yellow liquid (in toluene)
Density:0.95 g/mL at 25 °C
Melting point:85-95 ºC
Boiling point:111 °C
Flash point:40°F toluene
Hazards
 EU classification:  File:Highly flammable(F).jpg File:Hamful(Xn).jpg
 R-phrases:  R17

(R)-2-Methyl-CBS-oxazaborolidine is an oxazaborolidine reagent which mediates the enantioselective reduction of ketones previously developed by the laboratory of Itsuno, and thus this transformation may more properly be called the Itsuno-Corey oxazaborolidine reduction[2].  

References

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  1. ^ (R)-2-Methyl-CBS-oxazaborolidine at Viwit
  2. ^ Hirao, A.; Itsuno, S.; Nakahama, S.; Yamazaki, N. (1981), Journal of the Chemical Society, Chemical Communications 7: 315, doi:10.1039/C39810000315
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