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Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-METHYL-CBS-OXAZABOROLIDINE is used as a chiral catalyst for the synthesis of pharmaceuticals, enabling the creation of complex, chiral molecules with high enantioselectivity. This is vital for producing enantiomerically pure compounds, which are essential in the development of effective and safe drugs.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-2-METHYL-CBS-OXAZABOROLIDINE serves as a chiral catalyst for the synthesis of agrochemicals, ensuring the production of enantiomerically pure compounds. This is crucial for the development of effective and environmentally friendly pesticides and other agricultural chemicals.
Used in Material Science:
(R)-2-METHYL-CBS-OXAZABOROLIDINE is employed as a chiral catalyst in the development of new materials, contributing to the creation of innovative and advanced materials with unique properties. Its ability to promote stereoselective reactions aids in the synthesis of complex, chiral structures that are integral to the performance of these materials.
Used in Organic Chemistry Research:
As a chiral catalyst, (R)-2-METHYL-CBS-OXAZABOROLIDINE is used in organic chemistry research for asymmetric transformations, providing a means to achieve high enantioselectivity in various chemical reactions. This is particularly valuable in academic and industrial research settings, where the development of new synthetic methods and the exploration of novel chemical reactions are of significant interest.

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Chiral MeCBS synthesis process

The invention discloses a chiral MeCBS synthesis process. The process comprises the steps of adding 1.1-1.5 equivalent weight of methyl-boric acid in alkane solvent for back flow and water division, after the reaction is complete, lowering the temperature to 30-45 DEG C, after keeping static for filtration, lowering the filtered solution to below -20-0 DEG C, stirring and leaching out, after filtration and drying, acquiring the chiral MeCBS which is white solid with good fluidity. The processing method has the advantages of being simple in operation, being high in product purity, thus providing more choices in the current market with more available solvent types.

Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

Enantioselective reductive desymmetrization of glutarimides has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process that upgraded the enantioselectivity of an intermediate hydroxy-lactam. The reaction was generally tolerant of a number of substituents in the 4-position, giving enantiomeric excesses of greater than 82%.

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.

Rational electronic tuning of CBS catalyst for highly enantioselective borane reduction of trifluoroacetophenone

α,α,α-Trifluoroacetophenone (2), which is susceptible to noncatalytic reduction by BH3, could be reduced to chiral alcohol up to 90% ee by using electronically tuned-CBS catalyst (1) with BH3. The enantioselectivities highly correlated with the differential orbital energies between 1-BH3 adduct and 2, which were calculated by DFT method.

Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine

We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure, and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions. A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products could be predicted correctly in most cases (28 out of 30).

Process for the preparation of 1,3,2-oxazaborolidine compounds

A process is used for the preparation of 1,3,2-oxazaborolidine compounds. This process prepares compounds of formula (I) or (IA): in which: R1 is an alkyl or an aryl; and R2, R3, R4 and R5 are especially a hydrogen atom or an alkyl, wherein the following are reacted in two steps: a) a boric precursor compound with an acetal compound to give a boronate compound; and b) the boronate compound with an amino alcohol compound. This process avoids by-products and exhibits a very good stereospecificity.

Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis

The synthesis of the marine neurotoxin azaspiracid-1 has been accomplished. The individual fragments were synthesized by catalytic enantioselective processes: A hetero-Diels-Alder reaction to afford the E- and HI-ring fragments, a carbonyl-ene reaction to furnish the CD-ring fragment, and a Mukaiyama aldol reaction to deliver the FG-ring fragment. The subsequent fragment couplings were accomplished by aldol and sulfone anion methodologies. All ketalization events to form the nonacyclic target were accomplished under equilibrating conditions utilizing the imbedded configurations of the molecule to adopt one favored conformation. A final fragment coupling of the anomeric EFGHI-sulfone anion to the ABCD-aldehyde completed the convergent synthesis of (+)-azaspiracid-1.

First asymmetrie synthesis of frans-3,4-dimethyl-4-arylpiperidines

The first asymmetric synthesis of the trans-3,4-dimethyl-4-arylpiperidine opioid antagonist scaffold is reported. C-3 stereochemistry was established via CBS reduction and stereoselective anti-SN2′ cuprate displacement of the derived allylic phosphonate. The resultant vinyl bromide was then elaborated to the target compound by Suzuki coupling and frans-selective 4-methylation. Extension of this methodology should allow general enantioselective access to highly substituted piperidine ring systems.