The synthesis of new C2 symmetric bis(pyrrolidine-triazole)-based organocatalysts and their utility in the asymmetric Michael reaction of β-nitrostyrenes with very high diastereo- and enantioselectivity in water without any additives is reported. The asymmetric synthesis of nitrochromenes is also illustrated. © 2008 Elsevier Ltd. All rights reserved.

Sethuraman Sankararaman

Department Of Chemistry

Thandavamurthy Karthikeyan

carbon

chromene derivative

DRUG ADDITIVE

pyrrolidine derivative

styrene derivative

triazole

Water

article

catalyst

diastereoisomer

Enantioselectivity

Michael addition

priority journal

synthesis

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IIT Madras

Tetrahedron Asymmetry

In the tridentate ligand 2,6-bis(1-benzyl-1H-1,2,3-triazol-4-yl)pyridine, C23H19N7, both sets of triazole N atoms are anti with respect to the pyridine N atom, while in the copper complex aqua-[2,6-bis(1-benzyl-1H-1,2,3-triazol-4-yl)pyridine](pyridine) (tetra-fluoro-borato)copper(II) tetra-fluoro-borate, [Cu(BF4)(C 5H5N)(C23H19N7)(H 2O)]BF4, the triazole N atoms are in the syn-syn conformation. The coordination of the CuII atom is distorted octa-hedral. The ligand structure is stabilized through inter-molecular C - H⋯N inter-actions, while the crystal structure of the Cu complex is stabilized through water- and BF4-mediated hydrogen bonds. Photoluminiscence studies of the ligand and complex show that the ligand is fluorescent due to triazole-pyridine conjugation, but that the fluorescence is quenched on complexation. © 2010 International Union of Crystallography.

Acta Crystallographica Section C: Crystal Structure Communications

2,6-Bis(1-benzyl-1H-1,2,3-triazol-4-yl)pyridine and its octahedral copper complex

Chiral and achiral pincer type palladium complexes bearing abnormal N-heterocyclic carbene ligands derived from 1,2,3-triazole are reported. Both complexes are effective as catalysts for non-asymmetric Suzuki coupling reaction for the synthesis of biphenyl derivatives. However, both the complexes failed to catalyze the formation of binaphthyl derivatives, by the asymmetric Suzuki coupling in case of the chiral complex and the non-asymmetric version in case of the achiral pincer complex. Instead deboronation of arylboronic acid occurred very efficiently leaving the aryl bromide intact. © 2009 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

Palladium complexes with abnormal N-heterocyclic carbene ligands derived from 1,2,3-triazolium ions and their application in Suzuki coupling

Pyrrolidine-oxadiazolone based organocatalysts are envisaged, synthesized, and utilized for asymmetric Michael reactions. Results of the investigations suggest that some of the catalysts are indeed efficient for stereoselective 1,4-conjugated Michael additions (dr: >97:3, ee up to 99%) in high chemical yields (up to 97%) often in short reaction time. As an extension, one enantiopure Michael adduct has been utilized to synthesize optically active octahydroindole. © 2018 American Chemical Society.

Journal of Organic Chemistry

Pyrrolidine-Oxadiazolone Conjugates as Organocatalysts in Asymmetric Michael Reaction

Comprehensive Organic Name Reactions and Reagents

Hajos-Parrish-Eder-Sauer-Wiechert Reaction

Angewandte Chemie International Edition

Asymmetric Organocatalysis: From Infancy to Adolescence

Tetrahedron: Asymmetry

Silica-supported pyrrolidine–triazole, an insoluble, recyclable organocatalyst for the enantioselective Michael addition of ketones to nitroalkenes

Ionic-liquid-supported organocatalyst for the enantioselective Michael addition of ketones to nitroolefins

Organic Letters

Highly Enantioselective Michael Additions in Water Catalyzed by a PS-Supported Pyrrolidine

New pyrrolidine-triazole-based C2 symmetric organocatalysts and their utility in the asymmetric Michael reaction of β-nitrostyrenes and the synthesis of nitrochromenes

Journal	Tetrahedron Asymmetry
ISSN	09574166
Open Access	No