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649317

Sigma-Aldrich

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

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

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About This Item

Empirical Formula (Hill Notation):
C18H20BNO
CAS Number:
112022-83-0
Molecular Weight:
277.17
MDL number:
MFCD00078440
UNSPSC Code:
12352005
PubChem Substance ID:
24883644
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

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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Sing, V. K.
Synthesis, 605-605 (1992)
Current Science, 78, 1314-1317 (2000)
Corey, E. J. et al.
Journal of the American Chemical Society, 109, 5551-5551 (1987)
Angewandte Chemie (International Edition in English), 37, 1986-1986 (1998)
Sakai, T. et al.
Tetrahedron, 52, 233-233 (1996)
View All Related Papers

Articles

2-Methyl-CBS-oxazaborolidine

Our company is pleased to offer both enantiomers of 2-methyl-CBS-oxazaborolidine as a dry reagent, in addition to our current offerings as a 1 M solution in toluene.

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.

CBS Catalysts

We are pleased to offer o-tolyl-CBS-oxazaborolidine as a 0.5 M solution in toluene for your research needs. When protonated with trifluoromethanesulfonimide, these chiral oxazaborolidines generate chiral Lewis acids, which have demonstrated great utility in the enantioselective Diels–Alder reaction.

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