메뉴 건너뛰기




Volumn , Issue 4, 2005, Pages 646-649

Practical P-chiral phosphane ligand for Rh-catalyzed asymmetric hydrogenation

Author keywords

Alkenes; Asymmetric hydrogenation; P chiral phosphane ligand; Resolution; Rhodium

Indexed keywords

ALKANE DERIVATIVE; RHODIUM COMPLEX;

EID: 14944379368     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400690     Document Type: Article
Times cited : (174)

References (52)
  • 2
    • 0000701744 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
    • b) J. M. Brown, in: Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 121;
    • (1999) Comprehensive Asymmetric Catalysis , pp. 121
    • Brown, J.M.1
  • 8
    • 1542639278 scopus 로고
    • c) R. Noyori, Science 1990, 248, 1194;
    • (1990) Science , vol.248 , pp. 1194
    • Noyori, R.1
  • 25
    • 0037178489 scopus 로고    scopus 로고
    • and references cited therein
    • For P-chiral phosphorus ligands used in asymmetric hydrogenation, see: ref. [2], p. 3037 and references cited therein; and a) F. Maienza, F. Spindler, M. Thommen, B. Pugin, C. Malan, A. Mezzetti, J. Org. Chem. 2002, 67, 5239 and references cited therein;
    • (2002) J. Org. Chem. , vol.67 , pp. 5239
    • Maienza, F.1    Spindler, F.2    Thommen, M.3    Pugin, B.4    Malan, C.5    Mezzetti, A.6
  • 36
    • 2442618362 scopus 로고    scopus 로고
    • During the course of this investigation, a highly selective unsymmetrical P-chiral bis(trialkylphosphane) ligand was prepared in both enantiomeric forms by Pfizer research group, but in small scale using chiral preparatory HPLC, see: G. Hoge, H.-P. Wu, W. S. Kissel, D. A. Pflum, D. J. Greene, J. Bao, J. Am. Chem. Soc. 2004, 126, 5966.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5966
    • Hoge, G.1    Wu, H.-P.2    Kissel, W.S.3    Pflum, D.A.4    Greene, D.J.5    Bao, J.6
  • 45
    • 0033603422 scopus 로고    scopus 로고
    • Resolution of racemic phosphane oxide with (L)- or (D)-DBT was previously applied by Imamoto and Miura in the preparation of a dialkylaryl P-chiral phosphorus ligand, see: T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833. However, an attempt to resolve the corresponding racemic phosphane oxide intermediate of TangPhos failed due to the highly hygroscopic nature of that intermediate.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4833
    • Miura, T.1    Imamoto, T.2
  • 48
    • 14944349858 scopus 로고    scopus 로고
    • note
    • tert-Butylphosphane was prepared on lab scale by reduction of commercially available tert-butyldichlorophosphane with LAH. It can also be prepared on industrial scale from phosphane and isobutene.
  • 49
    • 14944361924 scopus 로고    scopus 로고
    • note
    • For a representation of the X-ray crystallography of the complex of (-)-6 and (D)-DBT, see Supporting Information. The X-ray crystallography data of this complex has been deposited with the Cambridge Crystallographic Data Centre (CCDC-257476). Experimental details of the ligand synthesis and a general hydrogenation procedure are also available included in the Supporting Information.
  • 52
    • 14944367076 scopus 로고    scopus 로고
    • note
    • It was found that an ether solution of DuanPhos was exposed to air for overnight without any oxidation detected.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.