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Volumn 70, Issue 18, 2005, Pages 7172-7178

Development of a new class of chiral phosphorus ligands: P-chirogenic diaminophosphine oxides. A unique source of enantioselection in Pd-catalyzed asymmetric construction of quaternary carbons

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; CATALYSTS; NITROGEN; PALLADIUM;

EID: 24144485814     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050800y     Document Type: Article
Times cited : (65)

References (73)
  • 2
    • 0003491250 scopus 로고
    • Sutherland, I. O. Ed.; Pergammon Press: Oxford
    • Barton, D.; Ollis, W. D. In Comprehensive Organic Chemistry; Sutherland, I. O. Ed.; Pergammon Press: Oxford, 1979; Vol. 2, Part 10.
    • (1979) Comprehensive Organic Chemistry , vol.2 , Issue.PART 10
    • Barton, D.1    Ollis, W.D.2
  • 29
    • 9244261559 scopus 로고    scopus 로고
    • Recent progress in transition metal catalysis using chiral and achiral phosphine oxides is highlighted in the following reference; see: Dubrovina, N. V.; Borner, A. Angew. Chem., Int. Ed. 2004, 43, 5883.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 5883
    • Dubrovina, N.V.1    Borner, A.2
  • 32
    • 33645605025 scopus 로고    scopus 로고
    • note
    • 6 is obtained as an air- and moisture-stable solid. The absolute configuration was unequivocally determined by X-ray crystal structure analysis. For detailed information of the X-ray analysis, see the Supporting Information of ref 9.
  • 45
    • 0033591944 scopus 로고    scopus 로고
    • For examples using α-monosubstituted ketones as the prochiral nucleophile, see: (a) Trost, B. M.; Schroeder, G. M. J. Am. Chem Soc. 1999, 121, 6759.
    • (1999) J. Am. Chem Soc. , vol.121 , pp. 6759
    • Trost, B.M.1    Schroeder, G.M.2
  • 52
    • 33645597966 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 53
    • 33645602989 scopus 로고    scopus 로고
    • note
    • In the case of acyclic nucleophiles, enantioselectivity was not affected by the addition of acetate salt. This result indicates that the source of enantioselection is different from that of cyclic nucleophiles. For detailed data, see Supporting Information.
  • 54
    • 0001948573 scopus 로고
    • Structure of 14 was confirmed by comparing the NMR data of an authentic sample, which was prepared according to the reported method using N,N-diethyltrimethylsilylamine. For reference, see: Plinta, H.-J.; Neda, I.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1995, 128, 695.
    • (1995) Chem. Ber. , vol.128 , pp. 695
    • Plinta, H.-J.1    Neda, I.2    Fischer, A.3    Jones, P.G.4    Schmutzler, R.5
  • 55
    • 33645591533 scopus 로고    scopus 로고
    • note
    • 2, 6, and BSA in a ratio of 1:2:60 (Pd:6 = 1:1) exhibited two singlet signals at 100.0 and 101.7 ppm. Although the corresponding structures have not been clarified, partial information has been obtained from the analytical experiments using 25 instead of 6. See Supporting Information for details.
  • 56
    • 33645585607 scopus 로고    scopus 로고
    • note
    • No trimethylsilylation of N-methylaniline occurred in the presence of excess BSA. This fact strongly supports our conclusion.
  • 61
    • 33645599751 scopus 로고    scopus 로고
    • note
    • 2 (10 mol %), 20 (1.5 equiv), BSA (2.5 equiv), toluene, rt]. For discussions about this result, see Supporting Information.
  • 62
    • 0001745314 scopus 로고
    • In the early 1980s, Negishi and co-workers reported their pioneering work on the Pd-catalyzed allylation of Zn enolates, where enolate nucleophiles attacked the π-allylpalladium species at the side opposite to the Pd metal. [For references, see: (a) Negishi, E.; Matsushita, H.; Chatterjee, S.; John, R. A. J. Org. Chem. 1982, 47, 3188.
    • (1982) J. Org. Chem. , vol.47 , pp. 3188
    • Negishi, E.1    Matsushita, H.2    Chatterjee, S.3    John, R.A.4
  • 64
    • 6844254916 scopus 로고    scopus 로고
    • For reviews, see: (a) Trost, B. M. Chem. Rev. 1996, 96, 395.
    • (1996) Chem. Rev. , vol.96 , pp. 395
    • Trost, B.M.1
  • 68
    • 33645605633 scopus 로고    scopus 로고
    • note
    • Diaminophosphine oxide 24 was prepared from (S)-glutamic acid; diaminophosphine oxides 25 and 26 were prepared from (S)-homophenylalanine. See Supporting Information for details.
  • 72
    • 0002355781 scopus 로고
    • It is known that coordination affinity of amines for Zn(II) species is dependent on the steric requirement of the amine rather than the amine basicity. In particular, tertiary amines such as triethylamine have extremely low coordination affinity compared with those of primary and secondary amines. [For references, see: (a) Higgins, G. M. C.; Saville, B. J. Chem. Soc. 1963, 2812.
    • (1963) J. Chem. Soc. , pp. 2812
    • Higgins, G.M.C.1    Saville, B.2
  • 73
    • 37049065622 scopus 로고
    • (b) Coates, E.; Rigg, B. Saville, B.; Skelton, D. J. Chem. Soc. 1965, 5613.] This information provides us with a reasonable explanation for the observed stereoselectivity in the reaction using 23 (Table 4, run 9), where the sidearm with a tertiary amine would be recognized as one of the steric elements, analogous to that of 25.
    • (1965) J. Chem. Soc. , pp. 5613
    • Coates, E.1    Rigg, B.2    Saville, B.3    Skelton, D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.