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Chiral bis(oxazoline) derivatives („BOX“) for catalytic applications abcr provides a series of bis(oxazoline) compounds („BOX“) which could be applied as ligands in a wide variety of enantioselective reactions. The excellent enantioselectivities show their enormous potential for synthetic procedures giving access to new structural motifs. ZnCl F F R1 + Br R2 N R2 R2 (DME)NiCl2 (5 mol-%) (S,S)-ligand (6 mol-%) (DME)NiCl (S,S)-ligand R) (6 mol-%) TMEDA (1.6 eq.) THF, 0°C TMEDA (1.6 eq.) THF, 0°C O up to 94% yield up to 94% yield F F R2 N O O R2 N N O Ph Ph (S,S)-ligand R1 „Nickel-Catalyzed Negishi Cross-Coupling of Bromodifluoroacetamides.“ A. Tarui, S. Shinohara, K. Sato, M. Omote, A. Ando, Organic Letters, 2016, 18(5), 1128-1131. ZnCl X R1 + F3C (DME)NiCl (S,S)-ligand (8 mol-% (DME)NiCl2 (6 mol-%) (S,S)-ligand (8 mol-%) ) R (S,S)-ligand (8 mol-%) alkyl alkyl THF, diglym -20° THF, diglyme -20°C alkyl CF3 R1 „Stereoconvergent Negishi Arylations of Racemic Secondary Alkyl Electrophiles: Differentiating between a CF3 and an Alkyl Group.“ Y. Liang, G. C. Fu, Journal of the American Chemical Society, 2015, 137(30), 9523-9526. SO2R NH H N O (R,R)-Catalyst (35 mol-%) MnO2 (3 eq.), Li2CO3 (2 eq.) ) (2 eq.) PhCF3, 115 °C, 24 h up to 86% yield up to 98% ee (S) isomer H SO2R N N O „Copper(II)-Catalyzed Enantioselective Intramolecular Cyclization of N-Alkenylureas.“ S. Fu, H. Yang, G. Li, Y. Deng, H. Jiang, W. Zeng, Organic Letters 2015, 17(4), 1018-1021. O O N N Ph Ph (S,S)-ligand O O N N Cu Ph Ph TfO OTf (R,R)-Catalyst Br alkyl RO O Co CoI2 (10 mol-%) (S,S)-ligand (12 mol-%) (S,S)-ligand (12 mol-% Aryl ) RO RO O O + ArylMgBr ArylMgBr THF, -80°C THF, -80°C up to 96% yield up to 97% ee (S) isomer up to 96% yield up to 97% ee (S) isomer up to 97% ee (S) isomer alkyl N N O Bn (S,S)-ligand Bn „Cobalt-Bisoxazoline-Catalyzed Asymmetric Kumada Cross-Coupling of Racemic α-Bromo Esters with Aryl Grignard Reagents.“ J. Mao, F. Liu, M. Wang, L. Wu, B. Zheng, S. Liu, J. Zhong, Q. Bian, P. J. Walsh, Journal of the American Chemical Society, 2014, 136(50), 17662-17668. Gute Chemie 1 7. 1 5 0 1. 0 4 3 7 4 NONO
AB171403 (R,R)-2,2‘-Isopropylidenebis(4-phenyl-2-oxazoline) 150529-93-4 AB150033 (-)-2,2-Bis[(4S)-4-phenyl-2-oxazolin-2-yl]propane; 98% 131457-46-0 AB331792 (R,R)-(+)-2,2‘-Isopropylidenebis(4-tert-butyl-2-oxazoline); 98% 131833-97-1 AB137494 (S,S)-(-)-2,2‘-Isopropylidenebis(4-tert-butyl-2-oxazoline); 95% 131833-93-7 AB471844 (R,R)-(-)-2,2‘-Isopropylidenebis(4-isopropyl-2-oxazoline) 150529-94-5 AB471845 (4S,4‘S)-2,2‘-(Propane-2,2-diyl)bis(4-isopropyl-4,5-dihydro- oxazole) 131833-92-6 AB471846 (4R,4‘R)-2,2‘-(Propane-2,2-diyl)bis(4-benzyl-4,5-dihydro- oxazole) 141362-77-8 AB471847 (4S,4‘S)-(-)-2,2‘-(1-Methylethylidene)bis[4,5-dihydro- 4-(phenylmethyl)oxazole] 176706-98-2 N N N N N N N N N N N N O O O O O O O O O O O O N N O O N N O O Gute Chemie
AB471848 (4R,4‘R)-2,2‘-(Pentane-3,3-diyl)bis(4-phenyl-4,5-dihydro- oxazole) 195515-48-1 AB471849 (4S,4‘S)-2,2‘-(Pentane-3,3-diyl)bis(4-phenyl-4,5-dihydro- oxazole) 190791-28-7 AB471850 (4R,4‘R)-2,2‘-(Pentane-3,3-diyl)bis(4-tert-butyl- 4,5-dihydrooxazole) 1332616-25-7 AB471851 (4S,4‘S)-2,2‘-(Pentane-3,3-diyl)bis(4-tert-butyl- 4,5-dihydrooxazole) 160191-66-2 AB471852 (4R,4‘R)-2,2‘-(Pentane-3,3-diyl)bis(4-isopropyl- 4,5-dihydrooxazole) 944706-09-6 AB471853 (4S,4‘S)-(-)-2,2‘-(3-Pentylidene)bis(4-isopropyloxazoline) 160191-65-1 AB471854 (4R,4‘R)-2,2‘-(Pentane-3,3-diyl)bis(4-benzyl-4,5-dihydro- oxazole) 1192345-90-6 AB471855 (4S,4‘S)-2,2‘-(Pentane-3,3-diyl)bis(4-benzyl-4,5-dihydro- oxazole) 160191-64-0 N N N N N N N N N N N N N N O O O O O O O O O O O O O O N N O O abcr GmbH · Phone +49 721 950 61 - 0 · Fax +49 721 950 61 - 80 · www.abcr.de · info@abcr.de
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