Synthesis of atropisomeric 1-phenylpyrrole-derived amino alcohols: New chiral ligands

Chirality

Volumn 24, Issue 7, 2012, Pages 532-542

  Faigl, Ferenc ^a,b   Mátrav̈olgyi, Beĺa ^b   Szöllosy, Áron ^a   Czugler, Mátyás ^b   Tárkányi, Gábor ^b   Vékey, Károly ^b   Kubinyi, Miklós ^b  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

Chiral amino alcohol; Enantioselective reaction; Metalation; Organocatalyst; Site selective reaction

Indexed keywords

1 [2 CARBOXY 6 (TRIFLUOROMETHYL)PHENYL] 1H PYRROLE 2 CARBOXYLIC ACID; 1 PHENYLPYRROLE; ALCOHOL; AMINOALCOHOL; ATROPISOMERIC AMINO ALCOHOL; BENZALDEHYDE; CARBOXYLIC ACID DERIVATIVE; CHIRAL LIGAND; DIETHYLZINC; LIGAND; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; OPTICAL RESOLUTION; PRIORITY JOURNAL; SYNTHESIS; X RAY DIFFRACTION;

AMINO ALCOHOLS; CHEMISTRY TECHNIQUES, SYNTHETIC; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OPTICAL PROCESSES; PYRROLES; ROTATION; STEREOISOMERISM; SUBSTRATE SPECIFICITY; THERMODYNAMICS; X-RAY DIFFRACTION;

EID: 84862904653     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22049     Document Type: Article

References (11)

1. Kocovsky P, Vyskocil S, Smrcina M. Non-symmetrically substituted 1,1′-binaphthyls in enantioselective catalysis. Chem Rev 2003;103:3213-3245.
2. Yang F, Xi P, Yang L, Lan J, Xie R, You J. Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis. J Org Chem 2007;72:5457-5460. (Pubitemid 47056248)
3. Montoya-Pelaez PJ, Uh YS, Lata C, Thompson MP, Lemieux RP, Crudden CM. The synthesis and resolution of 2,2′-, 4,4′-, and 6,6′-substituted chiral biphenyl derivatives for application in the preparation of chiral materials. J Org Chem 2006;71:5921-5929. (Pubitemid 44200259)
4. Faigl F, Tárkányi G, Fogassy K, Tepfenhart D, Thurner A. Synthesis and stereochemical stability of new atropisomeric 1-(substituted phenyl)pyrrole derivatives. Tetrahedron 2008;64:1371-1377.
5. Salehi P, Dabiri M, Kozehgary G, Baghbanzadeh M. An efficient method for catalytic enantioselective addition of diethylzinc to aryl aldehydes by a C2-symmetric chiral imino alcohol. Tetrahedron Asymmetry 2009;20:2609-2611.
6. Arroniz C, Escolano C, Luque FJ, Bosch J, Ama M. First asymmetric cascade reaction catalysed by chiral primary amino alcohols. Org Biomol Chem 2011;9:5079-5085.
7. Kasashima Y, Hanyu N, Aoki T, Mino T, Sakamoto M, Fujita T. Enantioselective addition of diethylzinc to aldehydes using novel chiral 1,4-aminoalcohols as chiral catalysts. J Oleo Sci 2005;9:495-504.
8. Brabander JH, Wright BW. Ring opening and defluorination of N-cyclopropyl-α,α,α-trifluoro-m-toluamide with lithium aluminum hydride. J Org Chem 1967;32(12):4053-4055.
9. Friebolin H. Basic One- and Two-Dimensional NMR Spectroscopy. Weinheim: Verlag Chemie; 1993. p 146, 155, 317, 320.
10. Faigl F, Thurner A, Tárkányi G, Kvári J, Mordini A. Resolution and enantioselective rearrangements of amino group containing oxiranyl ethers. Tetrahedron Asymmetry 2002;13:59-68. (Pubitemid 34219294)
11. Li Y, Zhou Y, Shi Q, Ding K, Noyori R, Sandoval CA. An efficient diphosphine/hybrid-amine combination for Ruthenium(II)-catalyzed asymmetric hydrogenation of aryl ketones. Adv Synth Catal 2011;353:495-500.