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Volumn 10, Issue 23, 1999, Pages 4501-4511

A new class of C2-symmetric diphosphine ligands derived from valine: Remarkably diverse behavior in catalytic asymmetric transformations

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; ALLYL COMPOUND; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; PHTHALIC ACID DERIVATIVE; RHODIUM; VALINE;

EID: 0033390074     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00520-0     Document Type: Article
Times cited : (35)

References (47)
  • 2
    • 0003544583 scopus 로고
    • (b) Ojima, I., Ed.; VCH: New York
    • (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
    • (1993) Catalytic Asymmetric Synthesis
  • 10
    • 0033588130 scopus 로고    scopus 로고
    • 2 and the isolation were examined according to a recent article, see:
    • +. According to the composition, a 1:1 complexation consisting of the bonding from two amide groups and the coordination of two phosphorus atoms was speculated. Thus, this unfavorable complexation has been proposed as a possible explanation for the unexpected behavior of 8b,c in palladium-catalyzed asymmetric allylic substitutions of 9. The presence of catalytically inactive palladium(II) complex with the similar type of coordination was pointed out in leading papers, see: Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545.
    • (1999) J. Org. Chem. , vol.64 , pp. 6247
    • Zhang, W.1    Shimanuki, T.2    Kida, T.3    Nakatsuji, Y.4    Ikeda, I.5    Trost, B.M.6    Toste, F.D.7
  • 11
    • 0040293452 scopus 로고    scopus 로고
    • 2 in benzene at room temperature under argon, followed by removing the volatile fractions in vacuo
    • +. According to the composition, a 1:1 complexation consisting of the bonding from two amide groups and the coordination of two phosphorus atoms was speculated. Thus, this unfavorable complexation has been proposed as a possible explanation for the unexpected behavior of 8b,c in palladium-catalyzed asymmetric allylic substitutions of 9. The presence of catalytically inactive palladium(II) complex with the similar type of coordination was pointed out in leading papers, see: Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 4545
    • Trost, B.M.1    Toste, F.D.2
  • 12
    • 0003905731 scopus 로고
    • (a) Morrison, J. D., Ed.; Academic Press: Orlando
    • (a) Ojima, I.; Hirai, K. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985.
    • (1985) Asymmetric Synthesis
    • Ojima, I.1    Hirai, K.2
  • 13
    • 85038056122 scopus 로고    scopus 로고
    • (b) in Ref. 1b. For reviews covering more recent articles, see
    • (b) Brunner, H.; Nishiyama, H.; Itoh, K. p. 303 in Ref. 1b. For reviews covering more recent articles, see:
    • Brunner, H.1    Nishiyama, H.2    Itoh, K.3
  • 16
    • 84985628211 scopus 로고
    • For instance, pyridinyloxazoline and its related ligands, see: (a)
    • For instance, pyridinyloxazoline and its related ligands, see: (a) Brunner, H.; Riepl, G.; Weitzer, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 331.
    • (1983) Angew. Chem., Int. Ed. Engl. , vol.22 , pp. 331
    • Brunner, H.1    Riepl, G.2    Weitzer, H.3
  • 27
    • 0030221030 scopus 로고    scopus 로고
    • (l) For phosphorous-containing oxazolines and other types of P-N ligands, see
    • (l) Imai, Y.; Zang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 2453. For phosphorous-containing oxazolines and other types of P-N ligands, see:
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 2453
    • Imai, Y.1    Zang, W.2    Kida, T.3    Nakatsuji, Y.4    Ikeda, I.5
  • 46
    • 85038070449 scopus 로고    scopus 로고
    • 9a The use of ligands with bulkier substituents led to the reduction of enantioselectivity in TRAP. However, TRAP is a different type of ligand system compared with the present ligands in terms of a relationship between a chiral center and a reactive site.
    • 9a The use of ligands with bulkier substituents led to the reduction of enantioselectivity in TRAP. However, TRAP is a different type of ligand system compared with the present ligands in terms of a relationship between a chiral center and a reactive site.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.