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Usage

Uses

Used in Pharmaceutical Industry:
Beta-Isocupreidine is used as a catalyst for the preparation of spiro-pyrrolidine-pyrazolone compounds, which are of significant interest in the pharmaceutical industry due to their potential therapeutic applications. The compound plays a crucial role in facilitating the synthesis of these bioactive molecules, contributing to the development of new drugs and treatments.

Upstream product

• 249731-47-3 quinine 9O-methanesulfonate 
• 130-95-0 quinine 
• 56-54-2 qunidine 
• 56-54-2 quinindine 
• 56-54-2 quinidine 
• 5056-73-5 (3R,8R,9S)-10,11-dihydro-3,9-epoxy-6'-methoxycinchonane 

Relevant academic research and scientific papers

Enantioselective Ammonium Ylide Mediated One-Pot Synthesis of Highly Substituted γ-Butyrolactones

An ammonium ylide mediated access towards trans-β,γ-disubstituted, all-trans-α,β,γ-trisubstituted, and α,α,β,γ-tetrasubstituted γ-butyrolactones bearing a broad variety of functionalities was developed. Starting from widely accessible benzylidene Meldrum's acid derivatives and α-bromo carbonyl compounds, γ-butyrolactones were obtained in yields between 32–99% with up to excellent diastereoselectivities (>95:5) via a DABCO-mediated [2+1] annulation. Utilization of enantiomerically pure cinchona alkaloid derivatives enables the first asymmetric ammonium ylide mediated method to provide (3R,?4R)-β,γ-disubstituted and (2R,?3R,?4R)-α,β,γ-trisubstituted γ-butyrolactones in moderate to good yields with up to very good enantiomeric ratios (97:3). The scalability of the transformation was proven while determining the absolute configuration. (Figure presented.).

Enantioselective α-hydroxylation of β-keto esters catalyzed by cinchona alkaloid derivatives

A highly efficient α-hydroxylation of β-keto esters catalyzed by cupreidine in the presence of cumyl hydroperoxide (CHP) was achieved. The reaction was applied to a wide variety of β-keto esters to give products in high yields (up to 95%) with excellent enantioselectivities (up to 97% ee). The reaction had been successfully scaled up to a gram quantity and (S)-5-chloro-2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate - the important intermediate of Indoxacarb were obtained in 96% yield with 86% ee. The enantiomeric excess could be improved to 99% by crystallization, and this method has prospect of industrial application for its advantages of enantioselectivity, ease of catalyst preparation and reclamation of catalyst. Georg Thieme Verlag Stuttgart. New York.

Tertiary amine-promoted enone aziridination: Investigations into factors influencing enantioselective induction

trans-N-Unsubstituted aziridines were synthesised (up to 77% ee) via a chiral tertiary amine-promoted nucleophilic aziridination of a,b-unsaturated ketones utilising in situ generated N-N ylides (aminimines). A wide range of chiral tertiary amines were sy

Organocatalytic asymmetric direct vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to nitroolefins

The first organocatalytic enantioselective direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactam to nitroolefins is developed using cinchona alkaloids as the catalysts. Both product enantiomers are accessible with moderate to good enantioselectivity.

Asymmetric synthesis of natural product inspired tricyclic benzopyrones by an organocatalyzed annulation reaction

(Chemical Equation Presented) Going back to nature: Electron-deficient oxadienes and electron-poor acetylene carboxylates react in the presence of an organocatalyst to give natural product inspired tricyclic benzopyrones efficiently (up to 99% yield) and

β-Isocupreidine-hexafluoroisopropyl acrylate method for asymmetric Baylis-Hillman reactions

Key features of the β-isocupreidine (β-ICD)-catalyzed asymmetric Baylis-Hillman reaction of aldehydes with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) are presented. In addition, an improved method using azeotropically dried β-ICD is described.