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457698

Sigma-Aldrich

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

1 M in toluene

Synonym(s):

α,α-Diphenyl-D-prolinolmethylboronic acid cyclamide ester, (R)-1-Methyl,3,3-diphenyl-tetrahydro-pyrrolo(1,2-c)(1,3,2)oxazaborole, (R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole

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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:
24869385
NACRES:
NA.22

concentration

1 M in toluene

bp

111 °C

density

0.95 g/mL at 25 °C

storage temp.

room temp

SMILES string

[H][C@]12CCCN1B(C)OC2(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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Application

CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
(R)-(+)-2-Methyl-CBS-oxazaborolidine solution [1M in toluene] may be used as a catalyst in the asymmetric borane reduction of perfluoroalkyl ketones.
It may also be used in the preparation of:
  • (-)-diospongin B
  • (1R)-2-azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol
  • (S)-α-deuteriobenzyl alcohol
  • (3S,4R,5S)-1-(trimethylsilyl)-4,5-epoxyhex-1-yn-3-ol
Excellent catalyst of asymmetric reductions.
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.
Used in a desymmetrizing reduction leading to (S)-4-hydroxycyclohexenone.

Physical form

Precipitate may form in storage, but does not affect product quality. Gently heat product to 80−90 °C under an inert atmosphere to redissolve solids.

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

39.2 °F - closed cup

Flash Point(C)

4 °C - closed cup

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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Enantiomeric resolution of fluorous mixture by chiral CD columns: asymmetric reduction of a mixture of fluorous ketones.
Nakamura Y, et al.
Tetrahedron Letters, 44(33), 6221-6225 (2003)
The discovery of long-acting saligenin ? 2 adrenergic receptor agonists incorporating hydantoin or uracil rings.
Procopiou PA, et al.
Bioorganic & Medicinal Chemistry, 19(14), 4192-4201 (2011)
Stereoselective glycosylations of a family of 6-deoxy-1, 2-glycals generated by catalytic alkynol cycloisomerization.
McDonald FE, et al.
Journal of the American Chemical Society, 122(18), 4304-4309 (2000)
Bis (oxazoline)-ligand-mediated asymmetric [2, 3]-Wittig rearrangement of benzyl ethers: reaction mechanism based on the hydrogen/deuterium exchange effect.
Kitamura M, et al.
Tetrahedron, 68(22), 4280-4285 (2012)
Synthesis, 2643-2643 (2006)
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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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