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649309

Sigma-Aldrich

(S)-(−)-2-Methyl-CBS-oxazaborolidine

≥95%

Synonym(s):

(S)-2-methyl-CBS-oxazaborolidine, (S)-CBS reagent, (S)-Me-CBS, (S)-Methyl-CBS

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About This Item

Empirical Formula (Hill Notation):
C18H20BNO
CAS Number:
112022-81-8
Molecular Weight:
277.17
MDL number:
MFCD00078439
UNSPSC Code:
12352005
PubChem Substance ID:
24883643
NACRES:
NA.22

Assay

≥95%

form

solid

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-/m0/s1

InChI key

VMKAFJQFKBASMU-KRWDZBQOSA-N

Related Categories

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.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H318

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Corey, E. J. et al.
Journal of the American Chemical Society, 109, 5551-5551 (1987)
Singh, 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)
E.J. Corey et al.
Tetrahedron Letters, 31, 611-611 (1990)
Cliff R Baar et al.
Journal of the American Chemical Society, 126(26), 8216-8231 (2004-07-01)
A series of enantiopure C1-symmetric metallocenes, [(SiMe2)2[eta5-C5H(CHMe2)2][eta5-C5H2((S)-CHMeCMe3)]]ZrCl2, (S)-2, [(SiMe2)2[eta5-C5H(CHEt2)2][eta5-C5H2((S)-CHMeCMe3)]]ZrCl2, (S)-6, and [(SiMe2)2[eta5-C5HCy2][eta5-C5H2((S)-CHMeCMe3)]]ZrCl2, (S)-7 (Cy = cyclohexyl), zirconocene dichlorides that have an enantiopure methylneopentyl substituent on the "upper" cyclopentadienyl ligand, and diastereomerically pure precatalysts, [(SiMe2)2[eta5-C5H((S)-CHMeCy)(CHMe2)][eta5-C5H3]]ZrCl2, (S)-8a and (S)-8b, which have an
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Articles

CBS Catalysts

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.

Asymmetric Catalysis with Chiral Oxazaborolidinium Ions (COBIs)

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.

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