메뉴 건너뛰기




Volumn 64, Issue 8, 1999, Pages 2737-2750

Molybdenum(II)- and tungsten(II)-catalyzed allylic substitution

Author keywords

[No Author keywords available]

Indexed keywords

MOLYBDENUM COMPLEX; TUNGSTEN DERIVATIVE;

EID: 0033574393     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9821776     Document Type: Article
Times cited : (61)

References (152)
  • 10
    • 0000636402 scopus 로고
    • For reviews, see: (d) Trost, B. M. Tetrahedron 1977, 33, 371.
    • (1977) Tetrahedron , vol.33 , pp. 371
    • Trost, B.M.1
  • 19
    • 2642670293 scopus 로고    scopus 로고
    • Precoordination to a neighboring group can also enforce the syn mechanism: (e) Farthing, C. N.; Kočovský, P. J. Am. Chem. Soc. 1998, 120, 6661.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6661
    • Farthing, C.N.1    Kočovský, P.2
  • 23
    • 85081225068 scopus 로고
    • For an overview of industrial applications of Pd, see: (d) Tsuji, J. Synthesis 1990, 739.
    • (1990) Synthesis , pp. 739
    • Tsuji, J.1
  • 25
    • 0041147514 scopus 로고
    • Attempts at developing the Pd(0)-catalyzed reaction of allylic esters with silyl enol ethers derived from simple ketones, as an extension of the established reactions with stabilized C-nucleophiles, have only met with modest success. In the examples reported to date, the more reactive carbonates (rather than acetates) have been employed and some of these reactions seem to work efficiently only as intramolecular processes: (a) Tsuji, J.; Minami, I.; Shimizu, I. Chemistry Lett. 1983, 1325.
    • (1983) Chemistry Lett. , pp. 1325
    • Tsuji, J.1    Minami, I.2    Shimizu, I.3
  • 48
    • 0344639705 scopus 로고    scopus 로고
    • note
    • Note that the opposite effect has been observed for the substrates in which the syn-mechanism is precluded by a steric bias so that the anti-mechanism (5) becomes the only possible pathway.11
  • 67
    • 0345501841 scopus 로고    scopus 로고
    • note
    • 22
  • 68
    • 0345501839 scopus 로고    scopus 로고
    • note
    • 2 at room temperature with 2-5 mol % of the catalyst and a slight excess (1,1 equiv) of the nucleophile. The reaction times and yields are given in Tables 1-6. All yields refer to "isolated" yields rather than "GC yields".
  • 69
    • 0028348463 scopus 로고
    • For a similar catalytic effect of Ce(IV) and/or Ce(III) on the transformation of allylic acetates or alcohols into the corresponding ethers on reaction with alcohols, see: (a) Iranpoor, N.; Mothaghineghad, E. Tetrahedron 1994, 50, 1859 and 7299.
    • (1994) Tetrahedron , vol.50 , pp. 1859
    • Iranpoor, N.1    Mothaghineghad, E.2
  • 72
    • 0001436414 scopus 로고
    • See also refs 8e,f
    • Enolates of β-dicarbonyls are known to form relatively stable chelate complexes with Mo(II): Brower, D. C.; Winston, P. B.; Tonker, T. L.; Templeton, J. L. Inorg. Chem. 1986, 25, 2883. See also refs 8e,f.
    • (1986) Inorg. Chem. , vol.25 , pp. 2883
    • Brower, D.C.1    Winston, P.B.2    Tonker, T.L.3    Templeton, J.L.4
  • 73
    • 0345501835 scopus 로고    scopus 로고
    • note
    • 3SiCl.
  • 78
    • 0344639684 scopus 로고    scopus 로고
    • note
    • 4a,e this is not the case with our Mo(II) catalysts, as revealed by analysis of the reaction mixtures at ∼50% conversion of 26 and 27 with MeOH and with 32. Hence, our results are not distorted by isomerization prior to the substitution reaction.
  • 79
    • 0344208116 scopus 로고    scopus 로고
    • note
    • D +36.9; ≥ 99% ee). However, this result could not be reproduced later. Painstaking analysis revealed that one batch of the starting ennatiomerically pure alcohol, used for the preparation of acetate (R)-(+)-23, was contaminated by ca. 5% of diisopropyl tartrate, originating from the Sharpless epoxidation (in kinetic resolution mode). Apparently, the tartrate, still present in the Mo(II)-catalyzed reaction, was the source of this error.
  • 88
    • 0001746712 scopus 로고
    • 2 have also been shown to be Lewis-acidic and, as such, to polymerize and/or rearrange olefins: Sen, A.; Thomas, R. R. Organometallics 1982, 1, 1251.
    • (1982) Organometallics , vol.1 , pp. 1251
    • Sen, A.1    Thomas, R.R.2
  • 89
    • 0000210530 scopus 로고    scopus 로고
    • For a recent, detailed discussion of the competing ionic and SET mechanism in the Mukaiyama-Michael reaction, and its dependence on the Lewis acid employed and the steric bulk of the reaction partners, see: Otera, J.; Fujita, Y.; Sakuta, N.; Fujita, M.; Fukuzumi, S. J. Org. Chem. 1996, 61, 2951.
    • (1996) J. Org. Chem. , vol.61 , pp. 2951
    • Otera, J.1    Fujita, Y.2    Sakuta, N.3    Fujita, M.4    Fukuzumi, S.5
  • 90
    • 0000258555 scopus 로고
    • For the Mo-and W-template-controlled allylic substitution, see refs 8-13. For the formation of a stable π-allyl complex on reaction of allyl chloride with 11a.b, see: Hull, C. G.; Stiddard, M. H. B. J. Organomet. Chem. 1967, 9, 519.
    • (1967) J. Organomet. Chem. , vol.9 , pp. 519
    • Hull, C.G.1    Stiddard, M.H.B.2
  • 91
    • 0001296153 scopus 로고
    • For related Fe-template-controlled reactions, see, e.g.: (a) Xu, Y.; Zhou, B. J. Org. Chem. 1987, 52, 974.
    • (1987) J. Org. Chem. , vol.52 , pp. 974
    • Xu, Y.1    Zhou, B.2
  • 110
    • 84943913171 scopus 로고
    • General references for the silyl enol ether formation (including 32, 35, 39, and 40) include ref 21a and the following: (a) Rathke, M. W.; Sullivan, D. F. Synth. Commun. 1973, 3, 67. 33:
    • (1973) Synth. Commun. , vol.3 , pp. 67
    • Rathke, M.W.1    Sullivan, D.F.2
  • 117
    • 0002652021 scopus 로고
    • Stereoselective alkylation reactions of chiral metal enolates
    • Morrison, J. D., Ed.; Academic: New York
    • (h) Evans, D. A. Stereoselective Alkylation Reactions of Chiral Metal Enolates. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1984; Vol. 3, p 1.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 1
    • Evans, D.A.1
  • 118
    • 0038746434 scopus 로고
    • Methoxy derivatives references are as follows. 43: ref 26 and (a) House, H. O.; Kniloch, B. F. J. Org. Chem. 1974, 39, 1173.
    • (1974) J. Org. Chem. , vol.39 , pp. 1173
    • House, H.O.1    Kniloch, B.F.2
  • 129
    • 0029061121 scopus 로고
    • References for products of the C-C bond formation are the following. 47: ref 46f. 49: (a) Laidig, G. J.; Hegedus, L. S. Synthesis 1995, 527.
    • (1995) Synthesis , pp. 527
    • Laidig, G.J.1    Hegedus, L.S.2
  • 139
    • 0010422691 scopus 로고
    • and references therein refs 48d,e. ref 48f
    • (k) Grieco, P. A.; Clark, J. D.; Jagoe, C. T. J. Am. Chem. Soc. 1991, 113, 5488 and references therein. 66: refs 48d,e. 67: ref 48f. 72:
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5488
    • Grieco, P.A.1    Clark, J.D.2    Jagoe, C.T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.