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Merck
CN

457698

(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
NACRES:
NA.22
PubChem Substance ID:
24869385
UNSPSC Code:
12352005
MDL number:
MFCD00078440

Key Documents

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Product Name

(R)-(+)-2-Methyl-CBS-oxazaborolidine solution, 1 M in toluene

Quality Level

200

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

SMILES string

[H][C@]12CCCN1B(C)OC2(c3ccccc3)c4ccccc4

InChI key

VMKAFJQFKBASMU-QGZVFWFLSA-N

concentration

1 M in toluene

bp

111 °C

density

0.95 g/mL at 25 °C

functional group

phenyl

storage temp.

room temp

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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.

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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

3 - Flammable liquids

wgk

WGK 3

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
易制毒化学品（3类）
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Certificates of Analysis (COA)

Lot/Batch Number
0000524016
0000524015
0000524015
0000524016
0000518999

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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)
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)
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)
Synthesis, 2643-2643 (2006)
Stereoselective synthesis of (-)-diospongins A and B and their stereoisomers at C-5.
Kawai N, et al.
Tetrahedron, 63(37), 9049-9056 (2007)
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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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