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Volumn 125, Issue 34, 2003, Pages 10219-10227

Synthesis of both enantiomers of a P-chirogenic 1,2-bisphospholanoethane ligand via convergent routes and application to rhodium-catalyzed asymmetric hydrogenation of CI-1008 (pregabalin)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS;

EID: 0042932780     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034715o     Document Type: Article
Times cited : (107)

References (54)
  • 2
    • 0000701744 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfalz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin
    • Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. I, pp 121-182.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 121-182
    • Brown, J.M.1
  • 12
    • 0041904956 scopus 로고    scopus 로고
    • note
    • STREM Chemicals currently offers research quantities of the DuPhos and BPE ligands and catalysts.
  • 17
    • 0042907027 scopus 로고    scopus 로고
    • note
    • Chiral Quest ligand.
  • 18
    • 0041904953 scopus 로고    scopus 로고
    • note
    • Solvias ligand.
  • 19
    • 0041904954 scopus 로고    scopus 로고
    • note
    • Chirotech Ligand.
  • 22
    • 0042406210 scopus 로고    scopus 로고
    • International publication number: WO 99/24444, filed 05/11/1998
    • This concept has been described in the patent literature. See: Berens, H. International publication number: WO 99/24444, filed 05/11/1998.
    • Berens, H.1
  • 23
    • 0042907025 scopus 로고    scopus 로고
    • note
    • It must also be pointed out that the phosphorous atom is rendered chiral because of the existence of stereogenic carbons in the phospholane ring. Therefore, while the described ligands are P-chirogenic, the stereogenic carbon atoms play the major role in defining the steric environment of the ligands and their corresponding rhodium catalysts.
  • 27
    • 0041749668 scopus 로고    scopus 로고
    • A similar P-chirogenic phospholane ligand was reported during the review process of this paper. See: Shimizu, H.; Saito, S.; Kumobayashi, H. Adv. Synth. Catal. 2003, 345, No. 1+2, 185.
    • (2003) Adv. Synth. Catal. , vol.345 , Issue.1-2 , pp. 185
    • Shimizu, H.1    Saito, S.2    Kumobayashi, H.3
  • 41
    • 0042907023 scopus 로고    scopus 로고
    • note
    • It is noteworthy that the 9:1 ratio of diastereomers 28 and 29 translates to 80% de. That compound 20 is produced in 77% ee is consistent with complete retention of configuration during the displacement of the menthoxy group with MeLi.
  • 44
    • 0041904949 scopus 로고    scopus 로고
    • note
    • We have also succeeded in synthesizing the racemic chiral diol on 1/2 kilogram scale via this route and then separating the enantiomers via SMB chromatography.
  • 50
    • 0042907024 scopus 로고    scopus 로고
    • note
    • It should be noted that substrates 39 and 40 are 1:5.7 E/Z mixtures and that the reaction rates and enantiomeric excesses observed at different reaction pressures might be different for each diastereomer. Pure E substrate could not be isolated for these comparisons, but we have observed that pure Z substrate follows the same enantioselectivity trends versus pressure as the 1:5.7 E/Z mixture.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.