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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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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)
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)
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.

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.

Related Content

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.

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