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Volumn , Issue 3, 2000, Pages 419-423

Synthesis of enantiomerically pure (-)-wine lactone based on a palladium-catalyzed enantioselective allylic substitution

Author keywords

Allylic substitution; Asymmetric synthesis; Natural products; Palladium; Wine lactone

Indexed keywords

LACTONE; PALLADIUM;

EID: 0033964331     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200002)2000:3<419::AID-EJOC419>3.0.CO;2-N     Document Type: Article
Times cited : (51)

References (32)
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    • Houben-Weyl E21
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    • [6c] T. Lubbers, P. Metz in Houben-Weyl E21, Stereoselective Synthesis (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), 1995, pp. 2371-2473 and 5643-5676.
    • (1995) Stereoselective Synthesis , pp. 2371-2473
    • Lubbers, T.1    Metz, P.2
  • 13
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    • note
    • 2-Cyclohen-1-yl chloride or bromide as substrates gave markedly lower enantioselectivity than the acetate.
  • 14
    • 0000960511 scopus 로고    scopus 로고
    • [8a] S. Kudis, G. Helmchen, Angew. Chem. 1998, 110, 3210-3212; Angew. Chem. Int. Ed. 1998, 37, 3047-3050.
    • (1998) Angew. Chem. , vol.110 , pp. 3210-3212
    • Kudis, S.1    Helmchen, G.2
  • 15
    • 0032538768 scopus 로고    scopus 로고
    • [8a] S. Kudis, G. Helmchen, Angew. Chem. 1998, 110, 3210-3212; Angew. Chem. Int. Ed. 1998, 37, 3047-3050.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3047-3050
  • 24
    • 0343262188 scopus 로고    scopus 로고
    • note
    • Alternatively, malonate (+)-3 was saponified and the resultant carboxylic acid decarboxylated by heating. This procedure caused formation of substantial amounts of side products and purification of the iodolactone was difficult.
  • 25
    • 0000902127 scopus 로고
    • The facility of purification of the iodolactone was independently found by us (ref.[7b]) and by the Scheffold group: T. Troxler, R. Scheffold, Helv. Chim. Acta 1994, 77, 1193-1202.
    • (1994) Helv. Chim. Acta , vol.77 , pp. 1193-1202
    • Troxler, T.1    Scheffold, R.2
  • 28
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    • Dissertation, Universität Würzburg
    • The choice of this CH-acid was based on previous work of our group: R. Wierzchowski, Dissertation, Universität Würzburg, 1985.
    • (1985)
    • Wierzchowski, R.1
  • 31
    • 0343697881 scopus 로고    scopus 로고
    • note
    • Using the same procedure ( + )-5 of 95% ee gave enantiomerically pure (-)-6 after recrystallization (yield: 82%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.