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457698 Aldrich

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

1 M in toluene

Synonym: 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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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Reduction
InChI Key   VMKAFJQFKBASMU-QGZVFWFLSA-N
concentration   1 M in toluene
bp   111 °C
density   0.95 g/mL at 25 °C
storage temp.   room temp

Description

Packaging

25 mL in Sure/Seal™

5 mL in glass bottle

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.

Application

(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

CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis

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.

Price and Availability

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN1294 - class 3 - PG 2 - Toluene, solution
WGK Germany 
3
Flash Point(F) 
39.2 °F
Flash Point(C) 
4 °C
Protocols & Articles

Articles

2-Methyl-CBS-oxazaborolidine

Since 1987, the series of chiral oxazaborolidines known as CBS catalysts (after the work of Corey, Bakshi, and Shibata) have been used for catalytic reduction of prochiral ketones,1 imines,2 and oxim...
ChemFiles Volume 5 Article 9
Keywords: Asymmetric synthesis, Catalysis, Crystallization, Reductions

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...
Aldrich ChemFiles 2005, 5.4, 2.
Keywords: Asymmetric synthesis, Catalysis, Chemfiles, 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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