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Volumn 355, Issue 8, 2013, Pages 1597-1604

Catalytic asymmetric hydrogenation of α-arylcyclohexanones and total synthesis of (-)-α-lycorane

Author keywords

Amarylliaceae alkaloids; asymmetric catalysis; chiral spiro catalyst; dynamic kinetic resolution; hydrogenation; lycorane

Indexed keywords


EID: 84878243721     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300165     Document Type: Article
Times cited : (41)

References (42)
  • 19
    • 38349079974 scopus 로고    scopus 로고
    • H. Pellissier, Tetrahedron 2008, 64, 1563. For selected recent papers on asymmetric hydrogenation of racemic α-substituted ketones via DKR, see
    • (2008) Tetrahedron , vol.64 , pp. 1563
    • Pellissier, H.1
  • 25
    • 4444287706 scopus 로고    scopus 로고
    • The cyclohexanone with an ethylene ketal group at its 3 position is sensitive under base conditions, forming 3-alkoxycyclohex-2-enone. See, T. K. M. Shing, C. M. Lee, H. Y. Ho, Tetrahedron 2004, 60, 9179. The poor solubility of 1a in i-PrOH is also a major reason for the formation of by-product 4a. The poor solubility of compound 1a in i-PrOH slows down the reaction rate of the hydrogenation. At the same time, the base-sensitive compound 1a is converted to by-product 4a. When toluene is added as a co-solvent, the solubility of compound 1a increases remarkably and the hydrogenation reaction speeds up. As a result, the formation of by-product 4a is suppressed.
    • (2004) Tetrahedron , vol.60 , pp. 9179
    • Shing, T.K.M.1    Lee, C.M.2    Ho, H.Y.3
  • 28
    • 77957083775 scopus 로고
    • in:; (Eds.: R. H. F. Manske, H. L. Holmes), Academic Press, New York, p 331
    • J. W. Cook, J. D. Loudon, in: The Alkaloids; (Eds.:, R. H. F. Manske, H. L. Holmes,), Academic Press, New York, 1952, Vol. 2, p 331
    • (1952) The Alkaloids , pp. 2
    • Cook, J.W.1    Loudon, J.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.