메뉴 건너뛰기




Volumn 9, Issue 22, 2003, Pages 5581-5596

Diamination of Olefins: Synthesis, Structures and Reactivity of Osmaimidazolidines

Author keywords

Diamination; Osmium; Stereoselective synthesis; Transition metal complexes

Indexed keywords

AMINATION; HYDROXYLATION; OSMIUM COMPOUNDS; X RAY ANALYSIS;

EID: 0345743713     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305011     Document Type: Article
Times cited : (57)

References (171)
  • 2
    • 0000341815 scopus 로고    scopus 로고
    • For a general review on chiral diamines: D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724; Angew. Chem. Int. Ed. 1998, 37, 2580.
    • (1998) Angew. Chem. , vol.110 , pp. 2724
    • Lucet, D.1    Le Gall, T.2    Mioskowski, C.3
  • 3
    • 0032538362 scopus 로고    scopus 로고
    • For a general review on chiral diamines: D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724; Angew. Chem. Int. Ed. 1998, 37, 2580.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2580
  • 4
    • 0001002139 scopus 로고    scopus 로고
    • For a review on trans-1,2-diamino cyclohexane and chiral derivatives thereof: Y. L. Bennani, S. Hanessian, Chem. Rev. 1997, 97, 3161.
    • (1997) Chem. Rev. , vol.97 , pp. 3161
    • Bennani, Y.L.1    Hanessian, S.2
  • 15
    • 0037463065 scopus 로고    scopus 로고
    • d) K. Kubota, J. L. Leighton, Angew. Chem. 2003, 115, 976; Angew. Chem. Int. Ed. 2003, 42, 946;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 946
  • 18
    • 37649026044 scopus 로고    scopus 로고
    • For outstanding examples of highly efficient asymmetric molecular catalysts containing chiral 1,2-diamines: a) R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 40; Angew. Chem. Int. Ed. 2001, 40, 40;
    • (2001) Angew. Chem. , vol.113 , pp. 40
    • Noyori, R.1    Ohkuma, T.2
  • 19
    • 37649026044 scopus 로고    scopus 로고
    • For outstanding examples of highly efficient asymmetric molecular catalysts containing chiral 1,2-diamines: a) R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 40; Angew. Chem. Int. Ed. 2001, 40, 40;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 40
  • 25
    • 0029989364 scopus 로고    scopus 로고
    • d) K. Hanabusa, M. Yamada, M. Kimura, H. Shirai, Angew. Chem. 1996, 108, 2086; Angew. Chem. Int. Ed. Engl. 1996, 35, 1949.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1949
  • 26
    • 0036456907 scopus 로고    scopus 로고
    • For an excellent schematic overview on synthetic routes: D. Enders, M. Meiers, Synthesis 2002, 2542.
    • (2002) Synthesis , pp. 2542
    • Enders, D.1    Meiers, M.2
  • 29
    • 0033519208 scopus 로고    scopus 로고
    • Selected examples: a) N. Taniguchi, T. Hata, M. Uemura, Angew. Chem. 1999, 111, 1311; Angew. Chem. Int. Ed. 1999, 38, 1232;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1232
  • 33
    • 0001429614 scopus 로고    scopus 로고
    • Selected examples: a) D. Enders, M. Meiers, Angew. Chem. 1996, 108, 2391; Angew. Chem. Int. Ed. Engl. 1996, 35, 2261;
    • (1996) Angew. Chem. , vol.108 , pp. 2391
    • Enders, D.1    Meiers, M.2
  • 34
    • 0030459043 scopus 로고    scopus 로고
    • Selected examples: a) D. Enders, M. Meiers, Angew. Chem. 1996, 108, 2391; Angew. Chem. Int. Ed. Engl. 1996, 35, 2261;
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2261
  • 35
    • 0141604467 scopus 로고    scopus 로고
    • b) B. Westermann, Angew. Chem. 2003, 115, 161; Angew. Chem. Int. Ed. 2003, 42, 151;
    • (2003) Angew. Chem. , vol.115 , pp. 161
    • Westermann, B.1
  • 36
    • 0037434136 scopus 로고    scopus 로고
    • b) B. Westermann, Angew. Chem. 2003, 115, 161; Angew. Chem. Int. Ed. 2003, 42, 151;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 151
  • 39
    • 0034680650 scopus 로고    scopus 로고
    • d) A. Alexakis, A. Tomassini, C. Chouillet, S. Roland, P. Mangeney, G. Bernardinelli, Angew. Chem. 2000, 112, 4259; Angew. Chem. Int. Ed. 2000, 39, 4093;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4093
  • 45
    • 0033523816 scopus 로고    scopus 로고
    • related diamine synthesis from racemic aziridinium compounds: c) T.-H. Chuang, K. B. Sharpless, Org. Lett. 1999, 1, 1435;
    • (1999) Org. Lett. , vol.1 , pp. 1435
    • Chuang, T.-H.1    Sharpless, K.B.2
  • 49
    • 0000096835 scopus 로고    scopus 로고
    • f) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056; Angew. Chem. Int. Ed. 2001, 40, 2004.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2004
  • 55
    • 0347266529 scopus 로고    scopus 로고
    • see also ref. [12c-f]
    • f) see also ref. [12c-f].
  • 69
    • 0346005532 scopus 로고
    • Tesis Doctoral, Zaragoza
    • b) F. Aznar, Tesis Doctoral, Zaragoza, 1975.
    • (1975)
    • Aznar, F.1
  • 74
    • 0347266525 scopus 로고    scopus 로고
    • note
    • c) Note, however, that all products from these reactions are achiral.
  • 79
    • 0035915127 scopus 로고    scopus 로고
    • a) G. Li, H.-X. Wei, S. H. Kim, M. Carducci, Angew. Chem. 2001, 113, 4407; Angew. Chem. Int. Ed. 2001, 40, 4277;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 4277
  • 94
    • 0347896830 scopus 로고    scopus 로고
    • note
    • An alternative interpretation consists of reversible or stepwise addition of 2 to the (Z)-configured olefin. Thus, an isomerization of the olefin geometry or of the internal C-C bond after addition of the first imino group might also be possible. However, this assumption does not explain the additional isomerisation after isolation of the mixture. The slow reaction rate and the low yield of this transformation made additional investigation rather complicated.
  • 103
    • 33748244629 scopus 로고
    • b) W. A. Herrmann, S. J. Eder, W. Scherer, Angew. Chem. 1992, 104, 1371; Angew. Chem. Int. Ed. Engl. 1992, 31, 1345;
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 1345
  • 105
    • 0347266521 scopus 로고    scopus 로고
    • note
    • d) further structures deposited at CCDC bear the following identification codes: OLATOS, QERCUL, MBAOOS, MTOLOS, OSOTYM, MAYDIZ, ADPYOS10, HOMMAX, HOMMEB and VIGPIK.
  • 107
    • 33748233298 scopus 로고
    • R. M. Pearlstein, B. K. Blackburn, M. W. Davis, K. B. Sharpless, Angew. Chem. 1990, 102, 710; Angew. Chem. Int. Ed. Engl. 1990, 29, 639.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 639
  • 118
    • 0031573889 scopus 로고    scopus 로고
    • A. E. Rubin, K. B. Sharpless, Angew. Chem. 1997, 109, 2751; Angew. Chem. Int. Ed. Engl. 1997, 36, 2637.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2637
  • 120
    • 0035903613 scopus 로고    scopus 로고
    • a) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3455
  • 123
    • 0036462501 scopus 로고    scopus 로고
    • c) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 472
  • 124
    • 0346005527 scopus 로고    scopus 로고
    • see also ref. [12f]
    • d) see also ref. [12f].
  • 125
    • 0029074988 scopus 로고
    • and references therein
    • The products obtained thereby are interesting derivatives of α,β-diamino acids that represent biologically interesting compounds. See, for example: Y. Nakamura, M. Hirai, K. Tamotsu, Y. Yonezawa, C.-G. Shin, Bull. Chem. Soc. Jpn. 1995, 68, 1369 and references therein.
    • (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 1369
    • Nakamura, Y.1    Hirai, M.2    Tamotsu, K.3    Yonezawa, Y.4    Shin, C.-G.5
  • 129
    • 0347896825 scopus 로고    scopus 로고
    • see also footnote [16] in ref. [21]
    • d) see also footnote [16] in ref. [21].
  • 131
    • 25044434957 scopus 로고    scopus 로고
    • unpublished results, Universität Bonn
    • K. Muñiz, unpublished results, Universität Bonn, 2002.
    • (2002)
    • Muñiz, K.1
  • 137
    • 0347266515 scopus 로고    scopus 로고
    • note
    • A single example of substrate-directed olefin diamination has been described by Barluenga et al. for the mercury-mediated diamination of (R)-limonene, albeit the reaction gave a product mixture.[23b]
  • 147
    • 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
  • 158
    • 33748983103 scopus 로고
    • Review: D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1059
  • 160
    • 0030984352 scopus 로고    scopus 로고
    • For the prime example: a) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297; Angew. Chem. Int. Ed. Engl. 1997. 36, 285;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 285
  • 170


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.