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Volumn 46, Issue 9, 2007, Pages 1497-1500

High enantioselectivity is induced by a single monodentate phosphoramidite ligand in iridium-catalyzed asymmetric hydrogenation

Author keywords

Asymmetric catalysis; Hydrogenation; Iridium; P ligands; Phosphoramidites

Indexed keywords

CATALYSIS; HYDROGENATION; IRIDIUM; PHOSPHORUS COMPOUNDS;

EID: 34247892462     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603930     Document Type: Article
Times cited : (75)

References (49)
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    • Eds, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Heidelberg
    • b) J. M. Brown in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 2004, p. 121;
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    • Eds, J. G. de Vries, C. J. Elsevier, Wiley-VCH, Weinheim
    • c) The Handbook of Homogeneous Hydrogenation (Eds.: J. G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim, 2007.
    • (2007) The Handbook of Homogeneous Hydrogenation
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    • f) J. G. de Vries in Handbook of Chiral Chemicals, 2nd ed. (Ed.: D. J. Ager), CRC, Boca Raton, FL, 2005, p. 269;
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    • To the best of our knowledge, there are only two earlier reports of the use of complexes with a chiral monodentate ligand to metal ratio of 1:1 as catalysts in asymmetric hydrogenation. The ee values obtained were low to moderate: a X. Jiang, A. J. Minnaard, B. Hessen, B. L. Feringa, A. L. L. Duchateau, J. G. O. Andrien, J. A. F. Boogers, J. G. de Vries, Org. Lett. 2003, 5, 1503;
    • To the best of our knowledge, there are only two earlier reports of the use of complexes with a chiral monodentate ligand to metal ratio of 1:1 as catalysts in asymmetric hydrogenation. The ee values obtained were low to moderate: a) X. Jiang, A. J. Minnaard, B. Hessen, B. L. Feringa, A. L. L. Duchateau, J. G. O. Andrien, J. A. F. Boogers, J. G. de Vries, Org. Lett. 2003, 5, 1503;
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    • 0033830964 scopus 로고    scopus 로고
    • A higher activity of the neutral complex with respect to the cationic one has also been reported for Ir/phosphonite catalysts in the hydrogenation of imines: A. Martorell, C. Claver, E. Fernandez, Inorg. Chem. Commun. 2000, 3, 132
    • A higher activity of the neutral complex with respect to the cationic one has also been reported for Ir/phosphonite catalysts in the hydrogenation of imines: A. Martorell, C. Claver, E. Fernandez, Inorg. Chem. Commun. 2000, 3, 132.
  • 33
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    • In all hydrogenation experiments the catalyst is formed in situ by simply mixing the Ir complex, the ligand, and the substrate prior to addition of the solvent. The results obtained with a preformed and isolated [Ir(cod)(Cl)L] catalyst are identical
    • In all hydrogenation experiments the catalyst is formed in situ by simply mixing the Ir complex, the ligand, and the substrate prior to addition of the solvent. The results obtained with a preformed and isolated [Ir(cod)(Cl)L] catalyst are identical.
  • 34
    • 1842681981 scopus 로고    scopus 로고
    • Phosphoramidites based on Biphen (3,3′-di-tert-butyl-5, 5′,6,6′-tetramethyl-1,1′-biphenyl-2,2′-diol) have already been prepared and used successfully in asymmetric hydroformylation: Z. Hua, V. C. Vassar, H. Choi, I. Ojima, Proc. Natl. Acad. Sci. USA 2004, 101, 5411.
    • Phosphoramidites based on Biphen (3,3′-di-tert-butyl-5, 5′,6,6′-tetramethyl-1,1′-biphenyl-2,2′-diol) have already been prepared and used successfully in asymmetric hydroformylation: Z. Hua, V. C. Vassar, H. Choi, I. Ojima, Proc. Natl. Acad. Sci. USA 2004, 101, 5411.
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    • See the Supporting Information
    • See the Supporting Information.
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    • For asymmetric hydrogenation of N-formyl-α-dehydroamino esters, see: L. Panella, A. M. Aleixandre, G. J. Kruidhof, J. Robertus, B. L. Feringa, J. G. de Vries, A. J. Minnaard, J. Org. Chem. 2006, 71, 2026.
    • For asymmetric hydrogenation of N-formyl-α-dehydroamino esters, see: L. Panella, A. M. Aleixandre, G. J. Kruidhof, J. Robertus, B. L. Feringa, J. G. de Vries, A. J. Minnaard, J. Org. Chem. 2006, 71, 2026.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.