674648
Aldrich

(S)-(−)-2-Methyl-CBS-oxazaborolidine solution

1 M in tetrahydrofuran

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Synonym

(S)-1-Methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2c][1,3,2]oxazaborole

(S)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole

(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole

α,α-Diphenyl-L-prolinol methylboronic acid cycl-amide ester

Molecular Formula

C₁₈H₂₀BNO

Molecular Weight

277.17

CAS Number

112022-81-8

MDL number

MFCD00078439

PubChem Substance ID

24885227

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Descriptions

Packaging

5, 25 mL in glass btl

Application

The CBS (Corey-Bakshi-Shibata) oxazaborolidine catalyst has been used in the asymmetric reduction of prochiral ketones.^1,^2,³ Other applications include the enantioselective synthesis of α-hydroxy acids,^4,⁵ α-amino acids,^6,⁷ C₂-symmetrical ferrocenyl diols,⁸ and propargyl alcohols.^9,¹⁰

Properties

concentration

1 M in tetrahydrofuran

refractive index

n20/D 1.460

density

0.942 g/mL at 25 °C

References

Cited Reference

1. Corey, E. J. et al. J. Am. Chem. Soc. 109, 5551, 7925, (1987)

2. Singh, V. K. Synthesis, 605, (1992)

3. Togni, A., Venanzi, L. M. Angew. Chem. Int. Ed. 33, 497, (1994)

4. Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 31, 611, (1990)

5. Corey, E. J.; Link, J. O. Tetrahedron Lett. 33, 3431, (1992)

6. Corey, E. J.; Link, J. O. J. Am. Chem. Soc. 114, 1906, (1992)

7. Sakai, T. et al. Tet. 52, 233, (1996)

8. Schwink, L.; Knochel, P. Tetrahedron Lett. 37, 25, (1996)

9. Parker, K. A.; Ledeboer, M. W. J. Org. Chem. 61, 3214, (1996) abstract

10. Stemmler, R.T. Synlett, 997, (2007)

Reference

Angew. Chem. Int. Ed. 37, 1986, (1998)

J. Am. Chem. Soc. 126, 8216-8231, (2004) abstract

Safety

Hazard Codes

F,Xi

Risk Statements

11-19-36/37/38

Safety Statements

16-26-29-33

RIDADR

UN 2056 3/PG 2

Flash Point(F)

5 °F

Flash Point(C)

-15 °C

Related Categories

... Chiral Catalysts, Ligands, and Reagents > Reduction

MSDS

Specification Sheet

Certificate of Analysis

More Information