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Volumn 72, Issue 19, 2007, Pages 7413-7416

t-Bu-QuinoxP* ligand: Applications in asymmetric Pd-catalyzed allylic substitution and Ru-catalyzed hydrogenation

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CHIRALITY; HYDROGENATION; KETONES; PALLADIUM COMPOUNDS; SUBSTITUTION REACTIONS;

EID: 34548735265     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071192k     Document Type: Article
Times cited : (55)

References (36)
  • 1
    • 0043240879 scopus 로고    scopus 로고
    • For representative reviews, see: a
    • For representative reviews, see: (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029-3069.
    • (2003) Chem. Rev , vol.103 , pp. 3029-3069
    • Tang, W.1    Zhang, X.2
  • 4
    • 0037012673 scopus 로고    scopus 로고
    • For recent representative examples, see: a
    • For recent representative examples, see: (a) Tang, W.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 1612-1614.
    • (2002) Angew. Chem., Int. Ed , vol.41 , pp. 1612-1614
    • Tang, W.1    Zhang, X.2
  • 24
    • 34548771185 scopus 로고    scopus 로고
    • Both enantiomers of t-Bu-QuinoxP* are commercially available from Aldrich Chemical Company. Imamoto, T, Sugita, K, Yoshida, K. U.S. Patent 2007021610, 2007; Imamoto, T, Sugita, K, Yoshida, K. JP Patent, 2007056007, 2007
    • Both enantiomers of t-Bu-QuinoxP* are commercially available from Aldrich Chemical Company. Imamoto, T.; Sugita, K.; Yoshida, K. U.S. Patent 2007021610, 2007; Imamoto, T.; Sugita, K.; Yoshida, K. JP Patent, 2007056007, 2007.
  • 28
    • 84891035198 scopus 로고    scopus 로고
    • de Vries, J. G, Elsevier, C. J, Eds, Wiley-VCH: Weinheim, Germany
    • Ohkuma, T.; Noyori, R. In Handbook of Homogeneous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, Germany, 2007; Vol. 3, pp 1105-1163.
    • (2007) Handbook of Homogeneous Hydrogenation , vol.3 , pp. 1105-1163
    • Ohkuma, T.1    Noyori, R.2
  • 29
    • 34548753391 scopus 로고    scopus 로고
    • The unit cell contained two Pd complexes and two dichloromethane molecules. One of the Pd complexes and the dichloromethane molecules are omited in Figure 1 and Table 1; CCDC 649473 for the compounds contains supplementary crystallographic data. The data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 IEZ, UK; fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
    • The unit cell contained two Pd complexes and two dichloromethane molecules. One of the Pd complexes and the dichloromethane molecules are omited in Figure 1 and Table 1; CCDC 649473 for the compounds contains supplementary crystallographic data. The data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 IEZ, UK; fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 32
    • 34548765998 scopus 로고    scopus 로고
    • It is known that C2-symmetric ligands are not so effective for Pd-catalyzed asymmetric allylic substitution as expected from their wide range of success in other catalytic asymmetric reactions; see ref 9
    • 2-symmetric ligands are not so effective for Pd-catalyzed asymmetric allylic substitution as expected from their wide range of success in other catalytic asymmetric reactions; see ref 9.
  • 34
    • 34548789567 scopus 로고    scopus 로고
    • Byproducts were observed only in the reaction of 3-oxo-3-arylpropionic acid ethyl esters having an electron-donating group on the aromatic ring. We found that the byproducts were formed by the reaction of produced alcohol 6 with EtOH in the presence of the t-Bu-QuinoxP*-Ru complex under the same conditions as those for the hydrogenation. Further, 6c also reacted with MeOH to give the 3-methoxy-3-(4′-methoxyphenyl)propionic acid ethyl ester. In the absence of hydrogen or Ru complex, no reaction occurred between 6c and alcohol.
    • Byproducts were observed only in the reaction of 3-oxo-3-arylpropionic acid ethyl esters having an electron-donating group on the aromatic ring. We found that the byproducts were formed by the reaction of produced alcohol 6 with EtOH in the presence of the t-Bu-QuinoxP*-Ru complex under the same conditions as those for the hydrogenation. Further, 6c also reacted with MeOH to give the 3-methoxy-3-(4′-methoxyphenyl)propionic acid ethyl ester. In the absence of hydrogen or Ru complex, no reaction occurred between 6c and alcohol.
  • 35
    • 0031562040 scopus 로고    scopus 로고
    • It is noted that hydrogenation product 6g (99.8% ee) is the key intermediate for epinephrine. See: Singer, R. A.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 927-930.
    • It is noted that hydrogenation product 6g (99.8% ee) is the key intermediate for epinephrine. See: Singer, R. A.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 927-930.
  • 36
    • 0023897616 scopus 로고    scopus 로고
    • It is noted that hydrogenation product 6i (99.2% ee) is the key intermediate for carnitine. See: Kitamura, M.; Ohkuma, T.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1988, 29, 1555-1556.
    • It is noted that hydrogenation product 6i (99.2% ee) is the key intermediate for carnitine. See: Kitamura, M.; Ohkuma, T.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1988, 29, 1555-1556.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.