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654299 Sigma-Aldrich

(R)-(+)-o-Tolyl-CBS-oxazaborolidine solution

0.5 M in toluene

Synonym: (R)-(+)-3,3-Diphenyl-1-o-tolyl-tetrahydropyrrolo(1,2-c)(1,3,2)oxazaborole

  • CAS Number 865812-10-8

  • Empirical Formula (Hill Notation) C24H24BNO

  • Molecular Weight 353.26

  •  MDL number MFCD07369781

  •  PubChem Substance ID 24884025

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Reduction
Quality Level   100
concentration   0.5 M in toluene
refractive index   n20/D 1.514
density   0.900 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-/m1/s1
InChI key   XHMKFCAQQGBIPZ-HSZRJFAPSA-N

Description

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.

Packaging

5, 25 mL in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Target organs 
Central nervous system
RIDADR 
UN1294 - class 3 - PG 2 - Toluene, solution
WGK Germany 
WGK 3
Flash Point(F) 
39.2 °F - closed cup - Not applicable
Flash Point(C) 
4 °C - closed cup - Not applicable
Protocols & Articles

Articles

CBS Catalysts for Chemical Synthesis, Materials List

. 2-Methyl-CBS-oxazaborolidines for asymmetric reduction . o-Tolyl-CBS-oxazaborolidines for asymmetric synthesis . Materials List
Keywords: Asymmetric synthesis, Catalysis, Diels-Alder reaction, Reductions

CBS Catalysts

Since 1987, the series of chiral oxazoborolidines known as CBS catalysts (after Corey, Bakshi, and Shibata) have been used for catalytic reduction of prochiral ketones,1 imines,2 and oximes3 to produ...
ChemFiles 2005, 5.4, 2.
Keywords: Asymmetric synthesis, Catalysis, Diels-Alder reaction, Reductions

CBS Oxazaborolidines

Since 1987, the series of chiral oxazaborolidines known as CBS catalysts (after Corey, Bakshi, and Shibata) have been used for the catalytic reduction of prochiral ketones, imines, and oximes to prod...
Aldrich ChemFiles 2007, 7.9, 20.
Keywords: Asymmetric synthesis, Catalysis, Chemfiles, Reductions

Related Content

CBS Catalysts for Asymmetric Reduction Synthesis

Since 1987, the series of chiral oxazoborolidines known as CBS catalysts (after the work of Corey, Bakshi, and Shibata) have been used for catalytic reduction of prochiral ketones¹, imines², and oxim...
Keywords: Asymmetric synthesis, Catalysis, Diels-Alder reaction, Reductions

Peer-Reviewed Papers
15

References

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