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654302

Sigma-Aldrich

(S)-(−)-o-Tolyl-CBS-oxazaborolidine solution

0.5 M in toluene

Synonym(s):

(S)-(−)-3,3-Diphenyl-1-o-tolyl-tetrahydropyrrolo(1,2-c)(1,3,2)oxazaborole solution

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About This Item

Empirical Formula (Hill Notation):
C24H24BNO
CAS Number:
463941-07-3
Molecular Weight:
353.26
MDL number:
MFCD07369782
UNSPSC Code:
12352005
PubChem Substance ID:
24884027
NACRES:
NA.22

concentration

0.5 M in toluene

density

0.9009 g/mL at 25 °C

SMILES string

[H][C@@]12CCCN1B(OC2(c3ccccc3)c4ccccc4)c5ccccc5C

InChI

1S/C24H24BNO/c1-19-11-8-9-16-22(19)25-26-18-10-17-23(26)24(27-25,20-12-4-2-5-13-20)21-14-6-3-7-15-21/h2-9,11-16,23H,10,17-18H2,1H3/t23-/m0/s1

InChI key

XHMKFCAQQGBIPZ-QHCPKHFHSA-N

Application

CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
When protonated with trifluoromethanesulfonimide, chiral oxazaborolidines generate chiral Lewis acids, which have demonstrated great utility in the enantioselective Diels-Alder reaction.[1][2]

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 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_germany

WGK 3

flash_point_f

39.2 °F - closed cup

flash_point_c

4.0 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBF4333V
SHBC6960
29296CM
72196DJ
10017PC

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Do Hyun Ryu et al.
Journal of the American Chemical Society, 125(21), 6388-6390 (2003-06-06)
The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.
Santanu Mukherjee et al.
Organic letters, 12(3), 632-635 (2010-01-13)
Diels-Alder reactions of various combinations of maleimides and 1,3-dienes with cationic oxazaborolidines as catalysts have been shown to be highly efficient and enantioselective.
Stemmler, R.T.
Synlett, 997-997 (2007)

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.

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