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649309 - (S)-(−)-2-Methyl-CBS-oxazaborolidine

649309 Aldrich

(S)-(−)-2-Methyl-CBS-oxazaborolidine

≥95.0%

CAS Number 112022-81-8
Empirical Formula (Hill Notation) C₁₈H₂₀BNO
Molecular Weight 277.17
MDL number MFCD00078439
PubChem Substance ID 24883643
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(S)-(−)-2-Methyl-CBS-oxazaborolidine ≥95.0%

Properties

Related Categories	Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Reduction
assay	≥95.0%

Description

Packaging

1, 10 g in glass bottle

Application

CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis

The CBS (Corey-Bakshi-Shibata) oxazaborolidine catalyst has been used in the asymmetric reduction of prochiral ketones. Other applications include the enantioselective synthesis of α-hydroxy acids, α-amino acids, C₂-symmetrical ferrocenyl diols, and propargyl alcohols.

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Related Papers

Asymmetric Reduction. A Convenient Method for the Reduction of Alkynyl Ketones. Parker, K. A.; Ledeboer, M. W. J. Org. Chem. 61, 3214, (1996)

Technical information & documentation associated with this product is available in the Safety & Documentation tab.

Articles

2-Methyl-CBS-oxazaborolidine

Since 1987, the series of chiral oxazaborolidines known as CBS catalysts (after the work of Corey, Bakshi, and Shibata) have been used for catalytic reduction of prochiral ketones,1 imines,2 and oxim...
ChemFiles Volume 5 Article 9
Keywords: Asymmetric synthesis, Catalysis, Crystallization, Reductions

CBS Catalysts in Chemical Synthesis

. 2-Methyl-CBS-oxazaborolidines for asymmetric reduction . o-Tolyl-CBS-oxazaborolidines for asymmetric synthesis . Materials List
Keywords: Asymmetric synthesis, Catalysis, Diels-Alder reaction, Reductions

CBS Catalysts

Since 1987, the series of chiral oxazoborolidines known as CBS catalysts (after Corey, Bakshi, and Shibata) have been used for catalytic reduction of prochiral ketones,1 imines,2 and oximes3 to produ...
Aldrich ChemFiles 2005, 5.4, 2.
Keywords: Asymmetric synthesis, Catalysis, Reductions

CBS Oxazaborolidines

Since 1987, the series of chiral oxazaborolidines known as CBS catalysts (after Corey, Bakshi, and Shibata) have been used for the catalytic reduction of prochiral ketones, imines, and oximes to prod...
Aldrich ChemFiles 2007, 7.9, 20.
Keywords: Asymmetric synthesis, Catalysis, Reductions

Papers

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Corey, E. J. et al. J. Am. Chem. Soc. 109, 5551, 925, (1987)

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

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

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

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

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

Sakai, T. et al. Tetrahedron 52, 233, (1996)

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

Asymmetric Reduction. A Convenient Method for the Reduction of Alkynyl Ketones. Parker, K. A.; Ledeboer, M. W. J. Org. Chem. 61, 3214, (1996)

Kinetic resolution of chiral alpha-olefins using optically active ansa-zirconocene polymerization catalysts. J. Am. Chem. Soc. 126, 8216-8231, (2004)

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

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

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