메뉴 건너뛰기




Volumn 5, Issue 3, 1999, Pages 883-896

First highly regio- and diastereoselective [3+2] cycloaddition of chiral nonracemic alkenyl Fischer carbene complexes with diazomethane derivatives: Preparation and synthetic applications of enantiomerically pure Δ2-pyrazolines

Author keywords

Amino alcohols; Azaprolines; Carbene complexes; Cycloadditions; Pyrazolines

Indexed keywords

DIAZOMETHANE; PYRAZOLINE DERIVATIVE;

EID: 0040610795     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990301)5:3<883::AID-CHEM883>3.0.CO;2-0     Document Type: Article
Times cited : (57)

References (83)
  • 2
    • 33746577674 scopus 로고
    • E. O. Fischer, A. Maasböl, Angew. Chem. 1964, 76,511; Angew. Chem. Int. Ed. Engl. 1964, 3, 580.
    • (1964) Angew. Chem. Int. Ed. Engl. , vol.3 , pp. 580
  • 3
    • 0038085207 scopus 로고
    • For reviews see: a) H.-G. Schmalz, Angew. Chem. 1994, 106, 311; Angew. Chem. Int. Ed. Engl. 1994, 33, 303;
    • (1994) Angew. Chem. , vol.106 , pp. 311
    • Schmalz, H.-G.1
  • 4
    • 33748226990 scopus 로고
    • For reviews see: a) H.-G. Schmalz, Angew. Chem. 1994, 106, 311; Angew. Chem. Int. Ed. Engl. 1994, 33, 303;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 303
  • 5
    • 0000134379 scopus 로고
    • (Eds.: E. W. Abbel, F. G. A. Stone, G. Wilkinson), Pergamon, New York
    • b) M. P. Doyle in Comprehensive Organometallic Synthesis II, Vol. 12 (Eds.: E. W. Abbel, F. G. A. Stone, G. Wilkinson), Pergamon, New York, 1995, p. 387;
    • (1995) Comprehensive Organometallic Synthesis II , vol.12 , pp. 387
    • Doyle, M.P.1
  • 6
    • 85033973468 scopus 로고    scopus 로고
    • W. D. Wulff in ref. [2b], p. 469
    • c) W. D. Wulff in ref. [2b], p. 469;
  • 7
    • 85033948389 scopus 로고    scopus 로고
    • L. S. Hegedus in ref. [2b], p. 549
    • d) L. S. Hegedus in ref. [2b], p. 549;
  • 17
    • 0000785117 scopus 로고
    • a) K. H. Dötz, Angew. Chem. 1984, 96, 573; Angew. Chem. Int. Ed. Engl. 1984, 23, 587;
    • (1984) Angew. Chem. , vol.96 , pp. 573
    • Dötz, K.H.1
  • 18
    • 84985559908 scopus 로고
    • a) K. H. Dötz, Angew. Chem. 1984, 96, 573; Angew. Chem. Int. Ed. Engl. 1984, 23, 587;
    • (1984) Angew. Chem. Int. Ed. Engl. , vol.23 , pp. 587
  • 22
    • 0023811387 scopus 로고
    • and references therein
    • For leading references, see: a) L. S. Hegedus, S. D'Andrea, J. Org. Chem. 1988, 53, 3113 and references therein;
    • (1988) J. Org. Chem. , vol.53 , pp. 3113
    • Hegedus, L.S.1    D'Andrea, S.2
  • 30
    • 0000533326 scopus 로고
    • (Eds.: B. M. Trost, T. Fleming), Pergamon, New York
    • a) W. D. Wulff, in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, T. Fleming), Pergamon, New York, 1991, p. 1065;
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1065
    • Wulff, W.D.1
  • 41
    • 0000629986 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon, New York
    • For reviews, see: a) A. Padwa, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 1069;
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1069
    • Padwa, A.1
  • 42
    • 85033944073 scopus 로고    scopus 로고
    • P. A. Wade, in ref. [9a], p. 1111
    • b) P. A. Wade, in ref. [9a], p. 1111;
  • 43
    • 85033967600 scopus 로고    scopus 로고
    • R. D. Little, in ref. [9a], Vol. 5, p. 239
    • c) R. D. Little, in ref. [9a], Vol. 5, p. 239;
  • 51
    • 84943407995 scopus 로고
    • (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Oxford
    • For a review, see: J. Elguero, in Comprehensive Heterocyclic Chemistry, Vol. 5 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, p. 167.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.5 , pp. 167
    • Elguero, J.1
  • 55
    • 0028795251 scopus 로고
    • and references therein
    • 1-pyrazolines, especially if they bear an electron-withdrawing group at the C3 position. For a recent example of this kind, see: G. Galley, M. Pätzel, P. G. Jones, Tetrahedron 1995, 51, 1631, and references therein.
    • (1995) Tetrahedron , vol.51 , pp. 1631
    • Galley, G.1    Pätzel, M.2    Jones, P.G.3
  • 56
    • 0030817559 scopus 로고    scopus 로고
    • 1-pyrazolines of type 5 to lose the silyl group in acidic media has been very recently demonstrated: a) M. R. Mish, F. M. Guerra, E. M. Carreira, J. Am. Chem. Soc. 1997,119, 8379;
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8379
    • Mish, M.R.1    Guerra, F.M.2    Carreira, E.M.3
  • 59
    • 33748226180 scopus 로고
    • a) J. Barluenga, J. M. Montserrat, J. Flórez, S. García-Granda, E. Martín, Angew. Chem. 1994, 106, 1451; Angew. Chem. Int. Ed. Engl. 1994, 33, 1392;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1392
  • 63
    • 85033957624 scopus 로고    scopus 로고
    • note
    • 5W] groups over oxygen in [3+2] cycloadditions, see refs. [11] and [12b].
  • 65
    • 85033958340 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures 8b and 14b reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications no. CCDC-102354 and 102355 respectively. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (Fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 66
    • 85033954510 scopus 로고    scopus 로고
    • note
    • -1, F(000) = 808, T=293(2)K. Final conventional R = 0.060 for 3211 observed reflections and ωR2 = 0.219 (for all reflections) and 498 variables, GoF = 1.00.
  • 69
    • 85033969764 scopus 로고    scopus 로고
    • see also ref. [15], p. 254
    • b) see also ref. [15], p. 254.
  • 70
    • 85033942006 scopus 로고    scopus 로고
    • note
    • 3/AcOH; see ref. [19a].
  • 71
    • 85033957116 scopus 로고    scopus 로고
    • note
    • At this stage, the enantiomeric purity of compounds 12 was verified by chiral HPLC analysis of derivatives 12b and 12c (ee>98%) on a Chiralcel OD-H column and n-hexane/ethanol (400:1) as eluent. This date confirms the high diastereoselectivity observed in the key [3+2] cycloaddition step of the transformation of 6 into 9.
  • 72
    • 0040538793 scopus 로고
    • (Eds.: D. Enders, R. Noyori, B. M. Trost), Thieme, New York
    • P. J. Kocienski, Protecting Groups (Eds.: D. Enders, R. Noyori, B. M. Trost), Thieme, New York, 1994, p. 2.
    • (1994) Protecting Groups , pp. 2
    • Kocienski, P.J.1
  • 73
    • 0001956304 scopus 로고
    • For recent reviews on the use of amino alcohols and diamines as chiral auxiliaries, see: a) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34; Angew. Chem. Int. Ed. Engl. 1991, 30, 49;
    • (1991) Angew. Chem. , vol.103 , pp. 34
    • Noyori, R.1    Kitamura, M.2
  • 74
    • 33745143561 scopus 로고
    • For recent reviews on the use of amino alcohols and diamines as chiral auxiliaries, see: a) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34; Angew. Chem. Int. Ed. Engl. 1991, 30, 49;
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 49
  • 81
    • 0002560113 scopus 로고
    • For the preparation of: a) diazomethane from Diazald®, see: T. H. Black, Aldrichimica Acta 1983,16, 3;
    • (1983) Aldrichimica Acta , vol.16 , pp. 3
    • Black, T.H.1
  • 82
    • 0003665556 scopus 로고
    • Thieme, Stuttgart
    • b) diazoarylderivatives, see: M. Regitz, Diazoalkanes, Thieme, Stuttgart, 1977 p. 121;
    • (1977) Diazoalkanes , pp. 121
    • Regitz, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.