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Volumn 43, Issue 4, 2004, Pages 514-517

Titanium(IV)-Catalyzed Dynamic Kinetic Asymmetric Transformation of Alcohols, Silyl Ethers, and Acetals under Carbon Allylation

Author keywords

Allylation; Asymmetric catalysis; C C coupling; Lewis acids; Nucleophilic substitution

Indexed keywords

ALCOHOLS; CARBON; CATALYSIS; OXYGEN; REACTION KINETICS;

EID: 0842307518     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352128     Document Type: Article
Times cited : (102)

References (53)
  • 10
    • 0030583519 scopus 로고    scopus 로고
    • P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623; J. V. Allen, J. M. J. Williams, Tetrahedron Lett. 1996, 37, 1859; M. T. Reetz, K. Schirnossek, Chimia 1996, 50, 668; A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. 1997, 109, 1256; Angew. Chem. Int. Ed. Engl. 1997, 36, 1211; R. Stürmer, Angew. Chem. 1997, 109, 1221; Angew. Chem. Int. Ed. Engl. 1997, 36, 1173, and references therein.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7623
    • Dinh, P.M.1    Howarth, J.A.2    Hudnott, A.R.3    Williams, J.M.J.4    Harris, W.5
  • 11
    • 0029968623 scopus 로고    scopus 로고
    • P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623; J. V. Allen, J. M. J. Williams, Tetrahedron Lett. 1996, 37, 1859; M. T. Reetz, K. Schirnossek, Chimia 1996, 50, 668; A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. 1997, 109, 1256; Angew. Chem. Int. Ed. Engl. 1997, 36, 1211; R. Stürmer, Angew. Chem. 1997, 109, 1221; Angew. Chem. Int. Ed. Engl. 1997, 36, 1173, and references therein.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1859
    • Allen, J.V.1    Williams, J.M.J.2
  • 12
    • 0001079960 scopus 로고    scopus 로고
    • P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623; J. V. Allen, J. M. J. Williams, Tetrahedron Lett. 1996, 37, 1859; M. T. Reetz, K. Schirnossek, Chimia 1996, 50, 668; A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. 1997, 109, 1256; Angew. Chem. Int. Ed. Engl. 1997, 36, 1211; R. Stürmer, Angew. Chem. 1997, 109, 1221; Angew. Chem. Int. Ed. Engl. 1997, 36, 1173, and references therein.
    • (1996) Chimia , vol.50 , pp. 668
    • Reetz, M.T.1    Schirnossek, K.2
  • 13
    • 0030583519 scopus 로고    scopus 로고
    • P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623; J. V. Allen, J. M. J. Williams, Tetrahedron Lett. 1996, 37, 1859; M. T. Reetz, K. Schirnossek, Chimia 1996, 50, 668; A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. 1997, 109, 1256; Angew. Chem. Int. Ed. Engl. 1997, 36, 1211; R. Stürmer, Angew. Chem. 1997, 109, 1221; Angew. Chem. Int. Ed. Engl. 1997, 36, 1173, and references therein.
    • (1997) Angew. Chem. , vol.109 , pp. 1256
    • Larsson, A.L.E.1    Persson, B.A.2    Bäckvall, J.-E.3
  • 14
    • 0030789621 scopus 로고    scopus 로고
    • P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623; J. V. Allen, J. M. J. Williams, Tetrahedron Lett. 1996, 37, 1859; M. T. Reetz, K. Schirnossek, Chimia 1996, 50, 668; A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. 1997, 109, 1256; Angew. Chem. Int. Ed. Engl. 1997, 36, 1211; R. Stürmer, Angew. Chem. 1997, 109, 1221; Angew. Chem. Int. Ed. Engl. 1997, 36, 1173, and references therein.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1211
  • 15
    • 0030583519 scopus 로고    scopus 로고
    • P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623; J. V. Allen, J. M. J. Williams, Tetrahedron Lett. 1996, 37, 1859; M. T. Reetz, K. Schirnossek, Chimia 1996, 50, 668; A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. 1997, 109, 1256; Angew. Chem. Int. Ed. Engl. 1997, 36, 1211; R. Stürmer, Angew. Chem. 1997, 109, 1221; Angew. Chem. Int. Ed. Engl. 1997, 36, 1173, and references therein.
    • (1997) Angew. Chem. , vol.109 , pp. 1221
    • Stürmer, R.1
  • 16
    • 0030751193 scopus 로고    scopus 로고
    • and references therein
    • P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623; J. V. Allen, J. M. J. Williams, Tetrahedron Lett. 1996, 37, 1859; M. T. Reetz, K. Schirnossek, Chimia 1996, 50, 668; A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. 1997, 109, 1256; Angew. Chem. Int. Ed. Engl. 1997, 36, 1211; R. Stürmer, Angew. Chem. 1997, 109, 1221; Angew. Chem. Int. Ed. Engl. 1997, 36, 1173, and references therein.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1173
  • 17
    • 37049067161 scopus 로고
    • S. G. Davies, D. Middlemiss, A. Naylor, M. Wills, J. Chem. Soc. Chem. Commun. 1990, 797; R. W. Hoffmann, T. Rühl, F. Chernla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719; D. S. Matteson, H.-W. Man, J. Org. Chem. 1994, 59, 5734; D. Enders, R. MaaBen, J. Runsink, Tetrahedron: Asymmetry 1998, 9, 2155; R. N. Ben, T. Durst, J. Org. Chem. 1999, 64, 7700; A. Kubo, H. Kubota, M. Takahashi, K. Nunami, J. Org. Chem. 1997, 62, 5830; P. N. Devine, U.-H. Dolling, R. M. Heid, Jr., D. M. Tschaen, Tetrahedron Lett. 1996, 37, 2683; T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023.
    • (1990) J. Chem. Soc. Chem. Commun. , pp. 797
    • Davies, S.G.1    Middlemiss, D.2    Naylor, A.3    Wills, M.4
  • 18
    • 84986676623 scopus 로고
    • S. G. Davies, D. Middlemiss, A. Naylor, M. Wills, J. Chem. Soc. Chem. Commun. 1990, 797; R. W. Hoffmann, T. Rühl, F. Chernla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719; D. S. Matteson, H.-W. Man, J. Org. Chem. 1994, 59, 5734; D. Enders, R. MaaBen, J. Runsink, Tetrahedron: Asymmetry 1998, 9, 2155; R. N. Ben, T. Durst, J. Org. Chem. 1999, 64, 7700; A. Kubo, H. Kubota, M. Takahashi, K. Nunami, J. Org. Chem. 1997, 62, 5830; P. N. Devine, U.-H. Dolling, R. M. Heid, Jr., D. M. Tschaen, Tetrahedron Lett. 1996, 37, 2683; T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023.
    • (1992) Liebigs Ann. Chem. , pp. 719
    • Hoffmann, R.W.1    Rühl, T.2    Chernla, F.3    Zahneisen, T.4
  • 19
    • 0000020176 scopus 로고
    • S. G. Davies, D. Middlemiss, A. Naylor, M. Wills, J. Chem. Soc. Chem. Commun. 1990, 797; R. W. Hoffmann, T. Rühl, F. Chernla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719; D. S. Matteson, H.-W. Man, J. Org. Chem. 1994, 59, 5734; D. Enders, R. MaaBen, J. Runsink, Tetrahedron: Asymmetry 1998, 9, 2155; R. N. Ben, T. Durst, J. Org. Chem. 1999, 64, 7700; A. Kubo, H. Kubota, M. Takahashi, K. Nunami, J. Org. Chem. 1997, 62, 5830; P. N. Devine, U.-H. Dolling, R. M. Heid, Jr., D. M. Tschaen, Tetrahedron Lett. 1996, 37, 2683; T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023.
    • (1994) J. Org. Chem. , vol.59 , pp. 5734
    • Matteson, D.S.1    Man, H.-W.2
  • 20
    • 0344110353 scopus 로고    scopus 로고
    • S. G. Davies, D. Middlemiss, A. Naylor, M. Wills, J. Chem. Soc. Chem. Commun. 1990, 797; R. W. Hoffmann, T. Rühl, F. Chernla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719; D. S. Matteson, H.-W. Man, J. Org. Chem. 1994, 59, 5734; D. Enders, R. MaaBen, J. Runsink, Tetrahedron: Asymmetry 1998, 9, 2155; R. N. Ben, T. Durst, J. Org. Chem. 1999, 64, 7700; A. Kubo, H. Kubota, M. Takahashi, K. Nunami, J. Org. Chem. 1997, 62, 5830; P. N. Devine, U.-H. Dolling, R. M. Heid, Jr., D. M. Tschaen, Tetrahedron Lett. 1996, 37, 2683; T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2155
    • Enders, D.1    MaaBen, R.2    Runsink, J.3
  • 21
    • 0032722407 scopus 로고    scopus 로고
    • S. G. Davies, D. Middlemiss, A. Naylor, M. Wills, J. Chem. Soc. Chem. Commun. 1990, 797; R. W. Hoffmann, T. Rühl, F. Chernla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719; D. S. Matteson, H.-W. Man, J. Org. Chem. 1994, 59, 5734; D. Enders, R. MaaBen, J. Runsink, Tetrahedron: Asymmetry 1998, 9, 2155; R. N. Ben, T. Durst, J. Org. Chem. 1999, 64, 7700; A. Kubo, H. Kubota, M. Takahashi, K. Nunami, J. Org. Chem. 1997, 62, 5830; P. N. Devine, U.-H. Dolling, R. M. Heid, Jr., D. M. Tschaen, Tetrahedron Lett. 1996, 37, 2683; T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023.
    • (1999) J. Org. Chem. , vol.64 , pp. 7700
    • Ben, R.N.1    Durst, T.2
  • 22
    • 0001365258 scopus 로고    scopus 로고
    • S. G. Davies, D. Middlemiss, A. Naylor, M. Wills, J. Chem. Soc. Chem. Commun. 1990, 797; R. W. Hoffmann, T. Rühl, F. Chernla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719; D. S. Matteson, H.-W. Man, J. Org. Chem. 1994, 59, 5734; D. Enders, R. MaaBen, J. Runsink, Tetrahedron: Asymmetry 1998, 9, 2155; R. N. Ben, T. Durst, J. Org. Chem. 1999, 64, 7700; A. Kubo, H. Kubota, M. Takahashi, K. Nunami, J. Org. Chem. 1997, 62, 5830; P. N. Devine, U.-H. Dolling, R. M. Heid, Jr., D. M. Tschaen, Tetrahedron Lett. 1996, 37, 2683; T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023.
    • (1997) J. Org. Chem. , vol.62 , pp. 5830
    • Kubo, A.1    Kubota, H.2    Takahashi, M.3    Nunami, K.4
  • 23
    • 0029928212 scopus 로고    scopus 로고
    • S. G. Davies, D. Middlemiss, A. Naylor, M. Wills, J. Chem. Soc. Chem. Commun. 1990, 797; R. W. Hoffmann, T. Rühl, F. Chernla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719; D. S. Matteson, H.-W. Man, J. Org. Chem. 1994, 59, 5734; D. Enders, R. MaaBen, J. Runsink, Tetrahedron: Asymmetry 1998, 9, 2155; R. N. Ben, T. Durst, J. Org. Chem. 1999, 64, 7700; A. Kubo, H. Kubota, M. Takahashi, K. Nunami, J. Org. Chem. 1997, 62, 5830; P. N. Devine, U.-H. Dolling, R. M. Heid, Jr., D. M. Tschaen, Tetrahedron Lett. 1996, 37, 2683; T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2683
    • Devine, P.N.1    Dolling, U.-H.2    Heid Jr., R.M.3    Tschaen, D.M.4
  • 24
    • 0009385805 scopus 로고
    • S. G. Davies, D. Middlemiss, A. Naylor, M. Wills, J. Chem. Soc. Chem. Commun. 1990, 797; R. W. Hoffmann, T. Rühl, F. Chernla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719; D. S. Matteson, H.-W. Man, J. Org. Chem. 1994, 59, 5734; D. Enders, R. MaaBen, J. Runsink, Tetrahedron: Asymmetry 1998, 9, 2155; R. N. Ben, T. Durst, J. Org. Chem. 1999, 64, 7700; A. Kubo, H. Kubota, M. Takahashi, K. Nunami, J. Org. Chem. 1997, 62, 5830; P. N. Devine, U.-H. Dolling, R. M. Heid, Jr., D. M. Tschaen, Tetrahedron Lett. 1996, 37, 2683; T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023.
    • (1995) Angew. Chem. , vol.107 , pp. 1099
    • Rein, T.1    Kreuder, R.2    Von Zezschwitz, P.3    Wulff, C.4    Reiser, O.5
  • 25
    • 33749098289 scopus 로고
    • S. G. Davies, D. Middlemiss, A. Naylor, M. Wills, J. Chem. Soc. Chem. Commun. 1990, 797; R. W. Hoffmann, T. Rühl, F. Chernla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719; D. S. Matteson, H.-W. Man, J. Org. Chem. 1994, 59, 5734; D. Enders, R. MaaBen, J. Runsink, Tetrahedron: Asymmetry 1998, 9, 2155; R. N. Ben, T. Durst, J. Org. Chem. 1999, 64, 7700; A. Kubo, H. Kubota, M. Takahashi, K. Nunami, J. Org. Chem. 1997, 62, 5830; P. N. Devine, U.-H. Dolling, R. M. Heid, Jr., D. M. Tschaen, Tetrahedron Lett. 1996, 37, 2683; T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1023
  • 28
    • 33745707470 scopus 로고    scopus 로고
    • a) R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 41; Angew. Chem. Int. Ed. 2001, 40, 40;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 40
  • 34
    • 0842299357 scopus 로고    scopus 로고
    • Reviews: E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 403; Angew. Chem. Int. Ed. 1998, 37, 388; J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725; Angew. Chem. Int. Ed. 2001, 40, 4591.
    • (1998) Angew. Chem. , vol.110 , pp. 403
    • Corey, E.J.1    Guzman-Perez, A.2
  • 35
    • 0032473509 scopus 로고    scopus 로고
    • Reviews: E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 403; Angew. Chem. Int. Ed. 1998, 37, 388; J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725; Angew. Chem. Int. Ed. 2001, 40, 4591.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 388
  • 36
    • 0001227615 scopus 로고    scopus 로고
    • Reviews: E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 403; Angew. Chem. Int. Ed. 1998, 37, 388; J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725; Angew. Chem. Int. Ed. 2001, 40, 4591.
    • (2001) Angew. Chem. , vol.113 , pp. 4725
    • Christoffers, J.1    Mann, A.2
  • 37
    • 0035905575 scopus 로고    scopus 로고
    • Reviews: E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 403; Angew. Chem. Int. Ed. 1998, 37, 388; J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725; Angew. Chem. Int. Ed. 2001, 40, 4591.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 4591
  • 39
    • 0842299356 scopus 로고
    • Dissertation, Universität Marburg
    • T. Seitz, Dissertation, Universität Marburg, 1988.
    • (1988)
    • Seitz, T.1
  • 43
    • 84961484227 scopus 로고
    • See: H. Sakurai, Pure Appl. Chem. 1982, 54, 1; I. Fleming, J. Dunoguès, R. Smithers, Org. React. 1989, 37, 57.
    • (1982) Pure Appl. Chem. , vol.54 , pp. 1
    • Sakurai, H.1
  • 45
    • 0004938625 scopus 로고
    • 3 (approximately 11 ppm); see: M. T. Reetz, M. Hüllmann, T. Seitz, Angew. Chem. 1987, 99, 478; Angew. Chem. Int. Ed. Engl. 1987, 26, 477, and references therein.
    • (1987) Angew. Chem. , vol.99 , pp. 478
    • Reetz, M.T.1    Hüllmann, M.2    Seitz, T.3
  • 46
    • 84985566340 scopus 로고
    • and references therein
    • 3 (approximately 11 ppm); see: M. T. Reetz, M. Hüllmann, T. Seitz, Angew. Chem. 1987, 99, 478; Angew. Chem. Int. Ed. Engl. 1987, 26, 477, and references therein.
    • (1987) Angew. Chem. Int. Ed. Engl. , vol.26 , pp. 477
  • 49
    • 0842320812 scopus 로고    scopus 로고
    • note
    • b) prepared by silylation of N-Cbz-protected 2-hydroxypiperidine.[13]


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