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Volumn 126, Issue 33, 2004, Pages 10248-10249

A palladium-catalyzed enantioselective alkylative desymmetrization of meso-succinic anhydrides

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOACID; ACID ANHYDRIDE; PALLADIUM; SUCCINIC ACID DERIVATIVE;

EID: 4143116743     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046528b     Document Type: Article
Times cited : (56)

References (27)
  • 4
    • 0027131552 scopus 로고
    • For the diastereoselective addition of aryl Grignard reagents to cyclic anhydrides, see: Real, S. D.; Kronenthal, D. R., Wu, H. Y. Tetrahedron Lett. 1993, 34, 8063-8066.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 8063-8066
    • Real, S.D.1    Kronenthal, D.R.2    Wu, H.Y.3
  • 8
    • 0033118177 scopus 로고    scopus 로고
    • (a) from acid chlorides, see: Dieter, R. K. Tetrahedron 1999, 55, 4177-4236.
    • (1999) Tetrahedron , vol.55 , pp. 4177-4236
    • Dieter, R.K.1
  • 9
    • 0032516391 scopus 로고    scopus 로고
    • (b) from thioesters, see: Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189-3192; Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260-11261; Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S.; Org. Lett. 2003, 5, 3033-3035.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3189-3192
    • Tokuyama, H.1    Yokoshima, S.2    Yamashita, T.3    Fukuyama, T.4
  • 10
    • 0034669524 scopus 로고    scopus 로고
    • (b) from thioesters, see: Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189-3192; Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260-11261; Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S.; Org. Lett. 2003, 5, 3033-3035.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11260-11261
    • Liebeskind, L.S.1    Srogl, J.2
  • 11
    • 0141855415 scopus 로고    scopus 로고
    • (b) from thioesters, see: Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189-3192; Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260-11261; Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S.; Org. Lett. 2003, 5, 3033-3035.
    • (2003) Org. Lett. , vol.5 , pp. 3033-3035
    • Wittenberg, R.1    Srogl, J.2    Egi, M.3    Liebeskind, L.S.4
  • 22
    • 4143143325 scopus 로고    scopus 로고
    • note
    • A control experiment performed in the absence of Pd provided <5% of 2.
  • 23
    • 4143114788 scopus 로고    scopus 로고
    • note
    • 2 = 38% ee.
  • 24
    • 4143127955 scopus 로고    scopus 로고
    • note
    • The absolute configuration of 2 is as shown and was determined by X-ray analysis of the corresponding iodolactonized ketone; all other compounds are assigned by analogy: see Supporting Information.
  • 26
    • 0032927129 scopus 로고    scopus 로고
    • We have observed dramatic effects of styrenic promoters in the nickel-catalyzed anhydride alkylation; see: ref 6. For use of olefins as reductive elimination promoters, see: Giovannini, R.; Studemann, T.; Devasagayaraj, A.; Dussin, G.; Knochel, P. J. Org. Chem. 1999, 64, 3544-3553.
    • (1999) J. Org. Chem. , vol.64 , pp. 3544-3553
    • Giovannini, R.1    Studemann, T.2    Devasagayaraj, A.3    Dussin, G.4    Knochel, P.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.