133261-83-3

Basic information

• Product Name: (R)-2-METHYL-CBS-OXAZABOROLIDINE
• Synonyms: ALPHA,ALPHA-DIPHENYL-D-PROLINOL METHYLBORONIC ACID CYCL-AMIDE-ESTER;(R)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C][1,3,2] OXAZABOROLE;(R)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C][1,3,2]OXAZOBOROLE;(R)-METHYL OXAZABOROLIDINE;(R)-ME CBS;(R)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE;(R)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-1H,3H-PYRROLO[1,2-C][1,3,2]OXAZABOROLE;(R)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-3H-PYRROLO-[1,2-C][1,3,2]OXAZABOROLE
• CAS NO: 133261-83-3
• Molecular Formula: C18H20BNO
• Molecular Weight: 277.17
• Mol File: 133261-83-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: 85-95 °C(lit.)
• Boiling Point: 111 °C
• Flash Point: 40 °F
• Appearance: /
• Density: 0.95 g/mL at 25 °C
• Storage Temp.: 2-8°C
• PKA: 1.02±0.40(Predicted)
• CAS DataBase Reference: (R)-2-METHYL-CBS-OXAZABOROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-METHYL-CBS-OXAZABOROLIDINE(133261-83-3)
• EPA Substance Registry System: (R)-2-METHYL-CBS-OXAZABOROLIDINE(133261-83-3)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-38-48/20-63-65-67
• Safety Statements: 36/37-62
• RIDADR: UN 1294 3/PG 2
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 133261-83-3(Hazardous Substances Data)

Usage

General Description

(R)-2-METHYL-CBS-OXAZABOROLIDINE is a chiral catalyst used in organic chemistry for asymmetric transformations. It is a boron-containing compound that has been shown to be effective in promoting a range of stereoselective reactions, such as asymmetric reductions and alkylations. The (R)-2-METHYL-CBS-OXAZABOROLIDINE has found applications in the synthesis of pharmaceuticals and agrochemicals, as well as in the development of new materials. Its unique structure and reactivity make it a valuable tool for the creation of complex, chiral molecules with high enantioselectivity.

Upstream product

• 22348-32-9 (S)-diphenylprolinol 
• 13061-96-6 dihydroxy-methyl-borane 
• 22348-32-9 (R)-α,α-diphenylprolinol 
• 823-96-1 Trimethylboroxine 
• 86595-28-0 methyldi-n-butoxyborane 
• 7318-81-2 bis(methoxy)methylborane 
• 151293-60-6 methylbis(diisopropylamino)borane 

Downstream Products

• 357405-40-4 (S)-α-(2-Chloroethyl)-5-isoxazolemethanol 
• 174060-40-3 3-[(2R)-oxiranyl]pyridine 
• 391906-07-3 (1R)-2-bromo-1-(3-pyridinyl)-1-ethanol 
• 1354227-36-3 C₁₀H₂₁NO₃ 
• 52780-14-0 (R)-1-(3-bromophenyl)ethanol 
• 76116-24-0 (R)-1-(3-nitrophenyl)ethanol 
• 530084-79-8 8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one 
• 202530-97-0 (R)-2-pentyl-2-cyclopentenol 

Relevant articles and documents

Efficient synthesis of (R)-phenylephrine using a polymer-supported Corey-Bakshi-Shibata catalyst

An efficient and mild synthetic route to (R)-phenylephrine hydrochloride using Corey-Bakshi-Shibata (CBS) catalyst was reported. In order to avoid a lengthy recovery process of the catalyst from homogeneous reaction, a polymer-supported CBS catalyst was prepared, and a preliminary attempt was made to achieve a continuous reduction on a laboratory scale, which contributes to synthesis of (R)-phenylephrine in a cost-effective way.

Stereospecific, Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Allylic Pivalates to Deliver Quaternary Stereocenters

Recognizing the importance of all-carbon, quaternary stereocenters in complex molecule synthesis, a stereospecific, nickel-catalyzed cross-coupling of allylic pivalates with arylboroxines to deliver products equipped with quaternary stereocenters and internal alkenes was developed. The enantioenriched allylic pivalate starting materials are readily prepared, and a variety of functional groups can be incorporated on both the allylic pivalate and the arylboroxine. Additional advantages include the use of a commercially available and air-stable Ni(II) salt and BISBI ligand, mild reaction conditions, and high yields and ee's. The observed stereoinversion of this reaction is consistent with an open transition state in the oxidative addition step.

Enantioselective catalytic desymmetrization of maleimides by temporary removal of an internal mirror plane and stereoablative over-reduction: Synthesis of (R)-pyrrolam A

A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product pyrrolam A.