51368-34-4

Usage

InChI:InChI=1/C5H10BrN.BrH/c6-4-5-2-1-3-7-5;/h5,7H,1-4H2;1H

Upstream product

• 147-85-3 L-proline 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 

Downstream Products

• 127075-51-8 (2S,αR)-N-(α-Methylbenzyl)-2-pyrrolidinmethansulfonsaeureamid 
• 127075-50-7 (S)-(+)-N-Benzyl-2-pyrrolidinmethansulfonsaeureamid 
• 127075-47-2 (S)-(+)-2-Pyrrolidinmethansulfonsaeure 

Relevant academic research and scientific papers

Chiral N-Heterocyclic Carbene Ligands Bearing a Pyridine Moiety for the Copper-Catalyzed Alkylation of N-Sulfonylimines with Dialkylzinc Reagents

Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99 % ee). The addition of HMPA to the reaction mixture as a co-solvent is critical in terms of chemical yield and enantioselectivity. A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction. Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99 % ee; see scheme). A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction.

2-[(Imidazolylthio)methyl]pyrrolidine as a trifunctional organocatalyst for the highly asymmetric Michael addition of ketones to nitroolefins

The direct asymmetric Michael addition of ketones to nitroolefins catalyzed by 2-[(imidazol-2-ylthio)methyl]pyrrolidine, constructed from natural L-proline and imidazolylthio platforms, with salicylic acid as a co-catalyst has been developed to give the products in high yields (up to 95%) and with excellent enantioselectivities (up to 99% ee). The highly efficient catalytic performance may be attributed to the dual activation of the Michael substrates by the trifunctional organocatalysts and the co-catalyst salicylic acid, leading to the formation of a stable transition state complex through the synergic effect of hydrogen-bonding and electrostatic interactions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Ion-supported chiral pyrrolidines as enantioselective catalysts for direct Michael addition of nitroalkenes in [BMIm]PF6

Imidazolium-supported-pyrrolidine-catalyzed asymmetric Michael addition reactions of unmodified ketones and aldehydes to nitroalkenes were performed in [BMIm]PF6 to give products in up to 98% yield and 99% enantioselectivity. The catalytic system presented a synergistic effect in the improvement of reaction performance and could be recycled. Georg Thieme Verlag Stuttgart.

Synthesis and properties of novel chiral-amine-functionalized ionic liquids

A novel class of chiral-amine-functionalized ionic liquids (CAFILs) has been synthesized efficiently from natural amino acids, and their structures have been determined by spectroscopic analysis and low temperature X-ray diffraction analysis. The CAFILs have been characterized by physical properties such as melting point, glass transition temperature, thermal degradation and specific rotation. NMR measurements indicate that the CAFILs may be promising alternatives in the field of chiral discrimination.

Bicyclic β-sultams: Synthesis from monocyclic β-aminothiols and some properties

The cyclamine methanethiols 7 are prepared from the corresponding alcohols 3 and oxidatively transformed by treatment with chlorine into the cyclic substituted taurinechlorides 8. Upon treatment with bases, 8 is cyclized yielding the bicyclic β-sultams 9. Some spectroscopic properties and the solvolysis of 9 are briefly discussed.