Asymmetric electrophilic amination of various carbon nucleophiles with enantiomerically pure chiral N-H oxaziridines derived from camphor and fenchone

Journal of Organic Chemistry

Volumn 67, Issue 22, 2002, Pages 7787-7796

  Page, Philip C Bulman ^a   Limousin, Corinne ^a   Murrell, Victor L ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILICITY;

AMINATION; CARBON; HYDROLYSIS; KETONES; NITROGEN; STEREOCHEMISTRY;

ESTERS;

CAMPHOR; CARBON; MALONIC ACID; NITRILE; NITROGEN; OXAZIRIDINE DERIVATIVE;

AMINATION; ARTICLE; CHIRALITY; ENANTIOMER; HYDROLYSIS; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY;

AMINATION; AZIRIDINES; CAMPHOR; CARBON; ESTERS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITRILES; NORBORNANES; STEREOISOMERISM;

EID: 0036828172     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020306j     Document Type: Article

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40. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
41. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
42. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
43. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
44. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
45. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
46. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
47. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
48. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
49. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
50. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
51. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
52. Recent reviews on electrophilic aminations: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. In Organic Synthesis Highlight; VCH Publishers: Weinheim, Germany, 1991; p 45. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Vol. E, 21e, Stereoselective Synthesis; Thieme Verlag: Stuttgart, Germany, 1995; p 5133. Greek, C.; Genet, J.-P. Synlett 1997, 741. See also: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. Erdik, E.; Daskapan, A. J. Chem. Soc., Perkin Trans. 1 1999, 3139. Bernardi, P.; Dembech, P.; Fabbri, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1999, 64, 641. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191. Gmeiner, P.; Bollinger, B. Liebigs Ann. Chem. 1992, 273. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. For asymmetric versions of electrophilic aminations see: Boche, G.; Schrott, W. Tetrahedron Lett. 1982, 23, 5403. Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 313, 991. Oppolzer, W.; Tamura, O. J. Am. Chem. Soc. 1992, 114, 5900. Genet, J.-P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. Carreira, E. M.; Hong, J.; Du Bois, J.; Tomooka, C. S. Pure Appl. Chem. 1998, 70, 1097. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. Greck, C.; Bischoff, L.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J.-P. Synlett 1993, 475. Seebach, D.; Sting, A. R. Tetrahedron 1996, 52, 279.
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