Atropos but Achiral Tris(phosphanyl)biphenyl Ligands for Ru-Catalyzed Asymmetric Hydrogenation

Angewandte Chemie - International Edition

Volumn 42, Issue 44, 2003, Pages 5455-5458

  Aikawa, Kohsuke ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Atropisomerism; Chirality; Hydrogenation; Phosphane ligands; Ruthenium

Indexed keywords

AMINES; CATALYSIS; ISOMERIZATION; RUTHENIUM;

AXIAL CHIRALITY; LIGANDS; RACEMIZATION;

HYDROGENATION;

BIPHENYL DERIVATIVE;

ARTICLE; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; HYDROGENATION; ISOMERISM; LIGAND BINDING; LOW TEMPERATURE;

EID: 0345305702     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352277     Document Type: Article

References (34)

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22. P-P = 5.3, 36.6 Hz, 1P).
23. P-P = 5.3, 42.8 Hz, 1P).
24. a) K. Mikami, T. Korenaga, T. Ohkuma, R. Noyori, Angew. Chem. 2000, 112, 3854-3857; Angew. Chem. Int. Ed. 2000, 39, 3707-3710;
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27. P-P = 6.2, 39.7 Hz, 1P).
28. Hydrogenation with enantiopure [binap-Ru-dpen]: a) for an excellent review, see: R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 40-75; Angew. Chem. Int. Ed. 2001, 40, 40-73;
29. Hydrogenation with enantiopure [binap-Ru-dpen]: a) for an excellent review, see: R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 40-75; Angew. Chem. Int. Ed. 2001, 40, 40-73;
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32. Examples of asymmetric hydrogenation: a) [(± )-tol-binap-Ru-(S,S)-dpen]: T. Ohkuma, H. Doucet, T. Pham, K. Mikami, T. Korenaga, M. Terada, R. Noyori, J. Am. Chem. Soc. 1998, 120, 1086-1087;
33. b) [(±)-dm(xyl)-binap-Ru-(S,S)-dpen]: K. Mikami, T. Korenaga, Y. Matsumoto, M. Ueki, M. Terada, S. Matsukawa, Pure. Appl. Chem. 2001, 73, 255-259.
34. We have already reported that a Ru complex with a 3,3′ -dimethyl-substituted biphep ligand (dm-biphep) can be controlled to a 3:1 diastereomeric ratio by enantiopure dpen. In asymmetric hydrogenation, the complex gave a higher enantioselectivity than the racemic dm-binap-Ru complex.[4a]