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Sigma-Aldrich

(R)-(+)-2-Methyl-CBS-oxazaborolidine

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Synonym(s):
(R)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole, (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole, (R)-Me-Corey-Bakshi-Shibata catalyst
Empirical Formula (Hill Notation):
C18H20BNO
CAS Number:
Molecular Weight:
277.17
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

≥90%

form

solid

mp

85-95 °C (lit.)

SMILES string

CB1OC(C2CCCN12)(c3ccccc3)c4ccccc4

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

InChI key

VMKAFJQFKBASMU-QGZVFWFLSA-N

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This Item
457698674656674648
Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

form

solid

form

-

form

-

form

-

mp

85-95 °C (lit.)

mp

-

mp

-

mp

-

Application

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.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Customers Also Viewed

Slide 1 of 3

1 of 3

Sing, V. K.
Synthesis, 605-605 (1992)
Asymmetric Reduction. A Convenient Method for the Reduction of Alkynyl Ketones.
Kathlyn A. Parker et al.
The Journal of organic chemistry, 61(9), 3214-3217 (1996-05-03)
Angewandte Chemie (International Edition in English), 37, 1986-1986 (1998)
Current Science, 78, 1314-1317 (2000)
Corey, E. J. et al.
Journal of the American Chemical Society, 109, 5551-5551 (1987)

Articles

we are pleased to offer both enatiomers of 2-methyl-CBS-oxazaborolidine as a dry reagent, in addition to our current offerings as a 1M solution in toluene.

Learn about the applications of chiral oxazaborolidinium ions (COBIs) as Lewis acid catalysts in different asymmetric reactions such as cyclopropanation, epoxidation, and radical reactions along with details of their catalytic action.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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