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Volumn 72, Issue 11, 1999, Pages 2491-2499

Room-temperature metallation of 2-substituted 1,3-dithiane derivatives and subsequent coupling with 2,3-disubstituted oxiranes

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE;

EID: 0032698793     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.2491     Document Type: Article
Times cited : (59)

References (65)
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  • 6
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    • 2-lithio-1,3-dithiane
    • ed by L. A. Paquette, John Wiley & Sons, Chichester
    • d) M. Kolb, "2-Lithio-1,3-dithiane," in "Encyclopedia of Reagents for Organic Synthesis," ed by L. A. Paquette, John Wiley & Sons, Chichester (1995), Vol. 5, pp. 2983-2989.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.5 , pp. 2983-2989
    • Kolb, M.1
  • 16
    • 0020395635 scopus 로고
    • For examples of the coupling reactions of 2-lithio-1,3-dithiane with 2,3-disubstituted oxiranes, see: a) M. Nakata, H. Enari, and M. Kinoshita, Bull. Chem. Soc. Jpn., 55, 3283 (1982).
    • (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 3283
    • Nakata, M.1    Enari, H.2    Kinoshita, M.3
  • 18
    • 0342931115 scopus 로고    scopus 로고
    • For only one example of the coupling of 2-substituted 2-lithio-1,3-dithiane derivative with 2,3-disubstituted oxirane, see: a) F. Sher, J. L. Isidor, H. R. Taneja, and R. M. Carlson. Tetrahedron Lett., 1973, 577. For three examples of the coupling of 2-aryl- and 2-vinyl-stabilized 2-lithio-1,3-dithiane derivatives with 2,3-disubstituted oxiranes. see:
    • Tetrahedron Lett. , vol.1973 , pp. 577
    • Sher, F.1    Isidor, J.L.2    Taneja, H.R.3    Carlson, R.M.4
  • 22
    • 0002708787 scopus 로고    scopus 로고
    • A portion of this research has been preliminarily reported: M. Ide, M. Yasuda, and M. Nakata, Synlett, 1998, 936.
    • Synlett , vol.1998 , pp. 936
    • Ide, M.1    Yasuda, M.2    Nakata, M.3
  • 29
    • 85038134872 scopus 로고    scopus 로고
    • note
    • The enantiomer of 9 was prepared by Smith et al., see Ref. 3h.
  • 32
    • 0018130646 scopus 로고
    • For examples of lithiation of 2-substituted 1,3-dithiane derivatives by n-BuLi or t-BuLi in the presence of HMPA, see: a) P.-E. Sum and L. Weiler, Can. J. Chem., 56, 2700 (1978).
    • (1978) Can. J. Chem. , vol.56 , pp. 2700
    • Sum, P.-E.1    Weiler, L.2
  • 42
    • 0028232294 scopus 로고
    • See also Refs. 3b, 3c, 3d, 3f, 3g, 3h, and 3i
    • k) H. J. Reich, J. P. Borst, and R. R. Dykstra, Tetrahedron, 50, 5869 (1994). See also Refs. 3b, 3c, 3d, 3f, 3g, 3h, and 3i.
    • (1994) Tetrahedron , vol.50 , pp. 5869
    • Reich, H.J.1    Borst, J.P.2    Dykstra, R.R.3
  • 44
    • 85038142413 scopus 로고    scopus 로고
    • note
    • Besides them. 1-(triphenylmethoxy)-3-buten-2-ol was produced as a by-product derived from oxirane 22 in less than 5% yield.
  • 45
    • 85038145357 scopus 로고    scopus 로고
    • note
    • In the structures of 23, 24, 25, 26, 31, 32, and 33, Me and OH substituents originated from 22 are arranged to syn.
  • 46
  • 58
    • 0009528834 scopus 로고
    • U. S. Patent 3847883 (1974)
    • 2Mg complex has been used, as a catalyst, for polymerization of monomers. For example, see: C. W. Kamienski, N. C. Gastonia, and J. F. Eastham, U. S. Patent 3847883 (1974); Chem. Abstr., 82, 58590 (1975).
    • (1975) Chem. Abstr. , vol.82 , pp. 58590
    • Kamienski, C.W.1    Gastonia, N.C.2    Eastham, J.F.3
  • 59
    • 0009531436 scopus 로고
    • European Patent 0491326A2
    • The same complex has been used for metallation of substituted trifluoromethylbenzenes, see: G. Castaldi and G. Borsotti. European Patent 0491326A2; Chem. Abstr., 117, 150667 (1992).
    • (1992) Chem. Abstr. , vol.117 , pp. 150667
    • Castaldi, G.1    Borsotti, G.2
  • 60
    • 0001466138 scopus 로고
    • The structure elucidation of diorganomagnesium organo-lithium complexes, see: a) L. M. Seitz and T. L. Brown, J. Am. Chem. Soc., 88, 4140 (1966).
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 4140
    • Seitz, L.M.1    Brown, T.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.