메뉴 건너뛰기




Volumn 5, Issue 6, 1999, Pages 1905-1916

Efficient desymmetrization of meso-cis-1,2-cyclohexanedimethanol with differentiation between diastereotopic and enantiotopic C-H bonds by (-)-sparteine-mediated deprotonation

Author keywords

Desymmetrization; Isotope effects; Kinetic resolution; Stereotopic differentiation

Indexed keywords

CARBAMIC ACID DERIVATIVE; CYCLOHEXANE DERIVATIVE; SPARTEINE;

EID: 0033047791     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990604)5:6<1905::AID-CHEM1905>3.0.CO;2-4     Document Type: Article
Times cited : (18)

References (105)
  • 3
    • 0000468225 scopus 로고    scopus 로고
    • c) D. E. Ward, Y. Liu, D. How, J. Am. Chem. Soc. 1996,118, 3025-3026; D. E. Ward, Y. Liu, D. How, J. Am. Chem. Soc. 1997, 119, 1884-1894;
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3025-3026
    • Ward, D.E.1    Liu, Y.2    How, D.3
  • 4
    • 0030887402 scopus 로고    scopus 로고
    • c) D. E. Ward, Y. Liu, D. How, J. Am. Chem. Soc. 1996,118, 3025-3026; D. E. Ward, Y. Liu, D. How, J. Am. Chem. Soc. 1997, 119, 1884-1894;
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1884-1894
    • Ward, D.E.1    Liu, Y.2    How, D.3
  • 15
    • 33748216597 scopus 로고
    • a) D. Seebach, G. Jaeschke, Y. M. Wang, Angew. Chem. 1995, 107, 2605-2606; Angew. Chem. Int. Ed. Engl. 1995, 34, 2395-2396;
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2395-2396
  • 22
    • 0343583098 scopus 로고
    • F. Hintze, P. Tebben, D. Hoppe, Angew. Chem. 1990, 102, 1457-1459; Angew. Chem. Int. Ed. Engl. 1990, 29, 1422-1423.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 1422-1423
  • 24
    • 0000854142 scopus 로고    scopus 로고
    • b) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2283-2316.
    • (1997) Angew. Chem. , vol.109 , pp. 2376-2410
    • Hoppe, D.1    Hense, T.2
  • 25
    • 0000129326 scopus 로고    scopus 로고
    • b) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2283-2316.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2283-2316
  • 29
    • 0029920726 scopus 로고    scopus 로고
    • A. Basu, P. Beak, J. Am. Chem. Soc. 1996, 118, 1575-1576; D. J. Gallagher, H. Du, S. A. Long, P. Beak, J. Am. Chem. Soc. 1996, 118, 11391-11398; G. A. Weisenberger, P. Beak, J. Am. Chem. Soc. 1996, 118, 12218-12219.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1575-1576
    • Basu, A.1    Beak, P.2
  • 30
    • 0029968950 scopus 로고    scopus 로고
    • A. Basu, P. Beak, J. Am. Chem. Soc. 1996, 118, 1575-1576; D. J. Gallagher, H. Du, S. A. Long, P. Beak, J. Am. Chem. Soc. 1996, 118, 11391-11398; G. A. Weisenberger, P. Beak, J. Am. Chem. Soc. 1996, 118, 12218-12219.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11391-11398
    • Gallagher, D.J.1    Du, H.2    Long, S.A.3    Beak, P.4
  • 31
    • 0030470857 scopus 로고    scopus 로고
    • A. Basu, P. Beak, J. Am. Chem. Soc. 1996, 118, 1575-1576; D. J. Gallagher, H. Du, S. A. Long, P. Beak, J. Am. Chem. Soc. 1996, 118, 11391-11398; G. A. Weisenberger, P. Beak, J. Am. Chem. Soc. 1996, 118, 12218-12219.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 12218-12219
    • Weisenberger, G.A.1    Beak, P.2
  • 34
    • 0001144369 scopus 로고
    • O. Zschage, J.-R. Schwark, D. Hoppe, Angew. Chem. 1990, 102, 336-337; Angew. Chem. Int. Ed. Engl. 1990, 29, 296-297; O. Zschage, J.-R. Schwark, T. Krämer, D. Hoppe, Tetrahedron 1992, 48, 8377-8388.
    • (1990) Angew. Chem. , vol.102 , pp. 336-337
    • Zschage, O.1    Schwark, J.-R.2    Hoppe, D.3
  • 35
    • 0025309871 scopus 로고
    • O. Zschage, J.-R. Schwark, D. Hoppe, Angew. Chem. 1990, 102, 336-337; Angew. Chem. Int. Ed. Engl. 1990, 29, 296-297; O. Zschage, J.-R. Schwark, T. Krämer, D. Hoppe, Tetrahedron 1992, 48, 8377-8388.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 296-297
  • 36
    • 0026754759 scopus 로고
    • O. Zschage, J.-R. Schwark, D. Hoppe, Angew. Chem. 1990, 102, 336-337; Angew. Chem. Int. Ed. Engl. 1990, 29, 296-297; O. Zschage, J.-R. Schwark, T. Krämer, D. Hoppe, Tetrahedron 1992, 48, 8377-8388.
    • (1992) Tetrahedron , vol.48 , pp. 8377-8388
    • Zschage, O.1    Schwark, J.-R.2    Krämer, T.3    Hoppe, D.4
  • 37
    • 0002240345 scopus 로고
    • a) J. Haller, T. Hense, D. Hoppe, Synlett 1993, 726-728; J. Haller, T. Hense, D. Hoppe, Liebigs Ann. Chem. 1996, 489-499;
    • (1993) Synlett , pp. 726-728
    • Haller, J.1    Hense, T.2    Hoppe, D.3
  • 41
    • 0002318553 scopus 로고    scopus 로고
    • D. M. Hodgson, G. P. Lee, Chem. Commun. 1996, 1015-1016; D. M. Hodgson, R. Wisedale, Tetrahedron Asymmetry 1996, 7, 1275-1276; D. M. Hodgson, A. R. Giggs, G. P. Lee, Tetrahedron 1996, 52, 14361-14384.
    • (1996) Chem. Commun. , pp. 1015-1016
    • Hodgson, D.M.1    Lee, G.P.2
  • 42
    • 0029942957 scopus 로고    scopus 로고
    • D. M. Hodgson, G. P. Lee, Chem. Commun. 1996, 1015-1016; D. M. Hodgson, R. Wisedale, Tetrahedron Asymmetry 1996, 7, 1275-1276; D. M. Hodgson, A. R. Giggs, G. P. Lee, Tetrahedron 1996, 52, 14361-14384.
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 1275-1276
    • Hodgson, D.M.1    Wisedale, R.2
  • 43
    • 0030580414 scopus 로고    scopus 로고
    • D. M. Hodgson, G. P. Lee, Chem. Commun. 1996, 1015-1016; D. M. Hodgson, R. Wisedale, Tetrahedron Asymmetry 1996, 7, 1275-1276; D. M. Hodgson, A. R. Giggs, G. P. Lee, Tetrahedron 1996, 52, 14361-14384.
    • (1996) Tetrahedron , vol.52 , pp. 14361-14384
    • Hodgson, D.M.1    Giggs, A.R.2    Lee, G.P.3
  • 50
    • 37049069133 scopus 로고
    • b) V. J. Jephcotre, A. J. Pratt, E. J. Thomas, J. Chem. Soc. Chem. Commun. 1984, 800-802; J. Chem. Soc. Perkin Trans, 1, 1989, 1529-1535;
    • (1989) J. Chem. Soc. Perkin Trans, 1 , pp. 1529-1535
  • 59
    • 84985530075 scopus 로고
    • S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-37.
    • (1985) Angew. Chem. Int. Ed. Engl. , vol.24 , pp. 1-37
  • 64
    • 84981969973 scopus 로고
    • D. Seebach, V. Prelog, Angew. Chem. 1982, 94, 696; Angew. Chem. Int. Ed. Engl. 1982, 21, 654.
    • (1982) Angew. Chem. Int. Ed. Engl. , vol.21 , pp. 654
  • 65
    • 0347548961 scopus 로고    scopus 로고
    • note
    • (R), which creates a doubly mismatched situation.
  • 68
    • 0343147529 scopus 로고
    • D. Hoppe, M. Paetow, F. Hintze, Angew. Chem. 1993, 105, 430-432; Angew. Chem. Int. Ed. Engl. 1993, 32, 394-396.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 394-396
  • 69
    • 0000005851 scopus 로고
    • B. Kaiser, D. Hoppe, Angew. Chem. 1995, 107, 344-346; Angew. Chem. Int. Ed. Engl. 1995, 34, 323-325; see also D. B. Reitz, P. Beak, R. F. Forney, L. S. Helmick, J. Am. Chem. Soc. 1978, 100, 5428-5436.
    • (1995) Angew. Chem. , vol.107 , pp. 344-346
    • Kaiser, B.1    Hoppe, D.2
  • 70
    • 33748242082 scopus 로고
    • B. Kaiser, D. Hoppe, Angew. Chem. 1995, 107, 344-346; Angew. Chem. Int. Ed. Engl. 1995, 34, 323-325; see also D. B. Reitz, P. Beak, R. F. Forney, L. S. Helmick, J. Am. Chem. Soc. 1978, 100, 5428-5436.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 323-325
  • 71
    • 0009648751 scopus 로고
    • B. Kaiser, D. Hoppe, Angew. Chem. 1995, 107, 344-346; Angew. Chem. Int. Ed. Engl. 1995, 34, 323-325; see also D. B. Reitz, P. Beak, R. F. Forney, L. S. Helmick, J. Am. Chem. Soc. 1978, 100, 5428-5436.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 5428-5436
    • Reitz, D.B.1    Beak, P.2    Forney, R.F.3    Helmick, L.S.4
  • 73
    • 33749120146 scopus 로고
    • W. Guarnieri, M. Grehl, D. Hoppe, Angew. Chem. 1994, 106, 1815-1818; Angew. Chem. Int. Ed. Engl. 1994, 33, 1734-1735.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1734-1735
  • 75
    • 0346917957 scopus 로고    scopus 로고
    • note
    • 1] = 93%).
  • 77
    • 0028238055 scopus 로고
    • For exceptions in benzylic cases see: a) A. Carstens, D. Hoppe, Tetrahedron 1994, 50, 6097-6108;
    • (1994) Tetrahedron , vol.50 , pp. 6097-6108
    • Carstens, A.1    Hoppe, D.2
  • 80
    • 0347548948 scopus 로고
    • Dissertation, Universität Münster
    • P. Sommerfeld, Dissertation, Universität Münster, 1995; P. Sommerfeld, D. Hoppe, Synlett 1992, 764-766; in ref. [8a].
    • (1995)
    • Sommerfeld, P.1
  • 81
    • 84985699791 scopus 로고
    • in ref. [8a]
    • P. Sommerfeld, Dissertation, Universität Münster, 1995; P. Sommerfeld, D. Hoppe, Synlett 1992, 764-766; in ref. [8a].
    • (1992) Synlett , pp. 764-766
    • Sommerfeld, P.1    Hoppe, D.2
  • 82
    • 0026062997 scopus 로고
    • Kinetic resolution of racemic stannanes by other methods, see: a) J. A. Marshall, D. V. Yashunsky, J. Org. Chem. 1991, 56, 5493-5495;
    • (1991) J. Org. Chem. , vol.56 , pp. 5493-5495
    • Marshall, J.A.1    Yashunsky, D.V.2
  • 84
    • 0346287771 scopus 로고    scopus 로고
    • note
    • If less than 1.5 equiv of MeLi/4 was applied, the yield of 11d was decreased.
  • 86
    • 0039208399 scopus 로고
    • b) J. Schwerdtfeger, D. Hoppe, Angew. Chem. 1992,104, 1547-1549; Angew. Chem. Int. Ed. Engl. 1992, 31, 1505-1507.
    • (1992) Angew. Chem. , vol.104 , pp. 1547-1549
    • Schwerdtfeger, J.1    Hoppe, D.2
  • 87
    • 0027074894 scopus 로고
    • b) J. Schwerdtfeger, D. Hoppe, Angew. Chem. 1992,104, 1547-1549; Angew. Chem. Int. Ed. Engl. 1992, 31, 1505-1507.
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 1505-1507
  • 90
    • 0002302741 scopus 로고
    • M.p.
    • M.p.: W. J. Close, J. Am. Chem. Soc. 1951, 73, 95-98; IR: S. Pinchas, D. Ben-Ishai, J. Am. Chem. Soc. 1957, 79, 4099-4104.
    • (1951) J. Am. Chem. Soc. , vol.73 , pp. 95-98
    • Close, W.J.1
  • 91
    • 33947463960 scopus 로고
    • IR
    • M.p.: W. J. Close, J. Am. Chem. Soc. 1951, 73, 95-98; IR: S. Pinchas, D. Ben-Ishai, J. Am. Chem. Soc. 1957, 79, 4099-4104.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 4099-4104
    • Pinchas, S.1    Ben-Ishai, D.2
  • 93
    • 0346917930 scopus 로고    scopus 로고
    • note
    • -3, hydrogens calculated and refined as riding atoms. Data set was collected with an Enraf-Nonius CAD4 diffractometer. Programs used: data reduction MolEN, structure solution SHELXS-86, structure refinement SHELXL-93, graphics SCHAKAL-92. Crystallographic data (excluding structure factors) for the structure reported in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100 883. 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).
  • 102
    • 0346917928 scopus 로고    scopus 로고
    • note
    • Surprisingly, according to a literature search in Chemical Abstracts, only racemic 24 has already been reported.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.