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Usage

Uses

Used in Pharmaceutical Industry:
(S,S)-(-)-2,2'-ISOPROPYLIDENEBIS(4-TERT-BUTYL-2-OXAZOLINE) is used as a chiral catalyst for asymmetric synthesis, enabling the production of enantiomerically pure compounds. This is crucial in the pharmaceutical industry, where the desired biological activity and reduced side effects are often associated with a specific enantiomer.
Used in Chemical Industry:
In the chemical industry, (S,S)-(-)-2,2'-ISOPROPYLIDENEBIS(4-TERT-BUTYL-2-OXAZOLINE) serves as a C2 symmetric ligand for enantioselective catalysis. Its ability to form bidentate coordination complexes with various metals enhances the efficiency and selectivity of catalytic processes, leading to the production of high-quality enantiomerically pure compounds.
Used in Research and Development:
(S,S)-(-)-2,2'-ISOPROPYLIDENEBIS(4-TERT-BUTYL-2-OXAZOLINE) is also utilized in research and development for the exploration of new catalytic systems and methodologies. Its unique properties and strong metal affinity make it an attractive candidate for the design and synthesis of novel chiral catalysts and ligands, further expanding its applications in various industries.

Upstream product

• 7321-55-3 2,2-dimethylmalononitrile 
• 112245-13-3 (S)-tert-leucinol 
• 2749-11-3 (S)-Alaninol 
• 3182-95-4 L-Phenylalaninol 
• 58577-87-0 O-benzyl-L-serinol 
• 20989-17-7 (2S)-2-phenylglycinol 
• 595-46-0 2,2-dimethylmalonic acid 
• 5659-93-8 2,2-Dimethylmalonyl chloride 
• 141-43-5 ethanolamine 
• 132098-54-5 (S,S)-2,2'-methylenebis(4-tert-butyl-2-oxazoline) 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Asymmetric hetero-Diels-Alder Reaction of trans-1-Methoxy-3-trimethylsilyloxy-buta-1,3-diene Catalyzed by Zinc Complexes

Asymmetric hetero-Diels-Alder reactions of Danishefsky's diene and glyoxylate/pyruvate esters catalyzed by readily available zinc triflate complex with BOX ligand afforded the corresponding adduct which upon treatment with trifluoroacetic acid furnished the hetero-Diels-Alder product in 91 % enantiomeric excess and 87 % isolated yield. This reaction was applied to the concise synthesis of six-membered ulosonic acid C-glycoside.

A catalytic asymmetric one-pot [3+2] cyclization/semipinacol rearrangement sequence: An efficient construction of a multi-substituted 3: H -spiro[benzofuran-2,1′-cyclopentane] skeleton

A facile and efficient method to form a chiral multi-substituted 3H-spiro[benzofuran-2,1′-cyclopentane] structural unit has been developed via a one-pot [3+2] cyclization/semipinacol rearrangement cascade. A catalysis system of Cu(ii)/BOX has been used to efficiently construct a key stereogenic center via a cyclization between substituted benzoquinones and allylic alcohols affording the desired products in good yields and with excellent enantioselectivities and diastereoselectivities (21 examples; up to 67% yields; up to 92% ee and up to >20:1 dr). This method provides an alternative strategy for the synthesis of the corresponding bioactive molecules containing spiro[benzofurancyclopentane] skeleton units.

Homogeneous asymmetric hydrogenation catalyst

Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.

Studies on the bisoxazoline- and (-)-sparteine-mediated enantioselective addition of organolithium reagents to imines

The enantioselective addition of organolithium reagents to N-anisylaldimines promoted by chiral bisoxazolines and (-)-sparteine as external ligands is described. This reaction proceeds readily with a wide range of aldimine substrates (aliphatic, aromatic, olefinic) and organolithium nucleophiles (Me, n-Bu, Ph, vinyl) in excellent yields (81-99%) and with high enantioselectivities (up to 97:3.0 er). The external ligands can be used in substoichiometric amounts albeit with slightly attenuated enantioselectivities. A systematic evaluation of the structural features of the bisoxazolines revealed a primary contribution from the substituent at C(4) and a secondary influence from the bridging substituents. A computational analysis (PM3) provided a clear rationalization for the origin of enantioselectivity.

Enantioselective synthesis of the C8-C20 segment of curvicollide C

The enantioselective synthesis of the C8-C20 fragment of curvicollide C has been accomplished. A catalytic asymmetric Claisen rearrangement (CAC), a diastereoselective methyl cupration of an alkynoate, and a Julia-Kocienski olefination served as key C/C-connecting transformations.

Synthesis of non-symmetric bisoxazoline compounds. An easy way to reach tailored chiral ligands

Bisoxazoline compounds have been used as chiral catalyst ligands in a wide variety of reactions. A great deal of effort has been aimed at the synthesis of C2-symmetric bisoxazolines but very few references exist for non-symmetric ones. As part of our studies into the possible usefulness of non-symmetric bisoxazolines, we report an easy method for the synthesis of bisoxazoline compounds bearing different substituents in each oxazoline ring.

An efficient and general one-pot method for the synthesis of chiral bis(oxazoline) and pyridine bis(oxazoline) ligands

An expeditious method for the synthesis of chiral box and pybox ligands is reported. The approach is based on a one-pot condensation reaction of chiral β-amino alcohols with a dinitrile using stoichiometric or catalytic amounts of zinc triflate. Yields gr