Following an ISES lead: The first examples of asymmetric Ni(0)-mediated allylic amination

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2661-2664

  Berkowitz, David B ^a   Maiti, Gourhari ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ENZYME INHIBITOR; GLYCINE; NICKEL; PHOSPHINE DERIVATIVE; VINYL DERIVATIVE;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CRYSTALLIZATION; DEPROTECTION REACTION; ENZYME ASSAY; REACTION ANALYSIS;

AMINATION; CATALYSIS; ENZYME INHIBITORS; GLYCINE; NICKEL; PHOSPHINES; PYRIDOXAL PHOSPHATE;

EID: 4344564985     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049159x     Document Type: Article

References (59)

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5. Inhibition studies: (a) Liang, F.; Kirsch, J. F. Biochemistry 2000, 39, 2436-2444. (b) Zheng, L.; White, R. H.; Cash, V. L.; Dean, D. R. Biochemistry 1994, 33, 4714-20. (c) Asada, Y.; Tanizawa, K.; Yonaha, K.; Soda, K. Agric. Biol. Chem. 1988, 52, 2873-2878. (d) Gehring, H.; Rando, R. R.; Christen, P. Biochemistry 1977, 16, 4832-4836. (e) Soper, T. S.; Manning, J. M.; Marcotte, P. A.; Walsh, C. T. J. Biol. Chem. 1977, 252, 1571-1575.
6. Inhibition studies: (a) Liang, F.; Kirsch, J. F. Biochemistry 2000, 39, 2436-2444. (b) Zheng, L.; White, R. H.; Cash, V. L.; Dean, D. R. Biochemistry 1994, 33, 4714-20. (c) Asada, Y.; Tanizawa, K.; Yonaha, K.; Soda, K. Agric. Biol. Chem. 1988, 52, 2873-2878. (d) Gehring, H.; Rando, R. R.; Christen, P. Biochemistry 1977, 16, 4832-4836. (e) Soper, T. S.; Manning, J. M.; Marcotte, P. A.; Walsh, C. T. J. Biol. Chem. 1977, 252, 1571-1575.
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10. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
11. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
12. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
13. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
14. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
15. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
16. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
17. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
18. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
19. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
20. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
21. L-Vinylglycine: (a) Rose, N. G. W.; Blaskovich, M. A.; Wong, A.; Lajoie, G. A. Tetrahedron 2001, 57, 1497-1507. (b) Campbell, A. D.; Raynam, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709. (c) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Synthesis 1997, 747-749 (d) Berkowitz, D. B.; Smith, M. K. Synthesis 1996, 39-41. (e) Griesbeck, A. G.; Hirt, J. Liebigs Ann. 1995, 1957-1961. (f) Hallinan, K. O.; Crout, D. H. G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537-3543. (g) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29-34. (h) Pellicciari, R.; Natalini, B.; Marinozzi, M. Synth. Commun. 1988, 18, 1715-1721. (i) Duhamel, L.; Duhamel, P.; Fouquay, S.; Eddine, J. J.; Peschard, O.; Plaquevent, J. C.; Ravard, A.; Solliard, R.; Valnot, J. Y.; Vincens, H. Tetrahedron 1988, 44, 5495-5506. (j) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thierry, J. Tetrahedron 1985, 41, 4347-4357. (g) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425-1428. (h) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron, 1984, 40, 1409-1417.
22. S)-Vigabatrin: (a) Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413. (b) Masson, G.; Zeghida, W.; Cividino, P.; Py, S.; Vallee, Y. Synlett 2003, 1527-1529. (c) Chandrasekhar, S.; Mohapatra, S. Tetrahedron Lett. 1998, 39, 6415-6418. (d) Alcón, M.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 2967-2974. (e) Wei, Z.-Y.; Knaus, E. E. Tetrahedron 1994, 50, 5569-78. (f) Wei, Z. Y.; Knaus, E. E. J. Org. Chem. 1993, 58, 1586-8.
23. S)-Vigabatrin: (a) Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413. (b) Masson, G.; Zeghida, W.; Cividino, P.; Py, S.; Vallee, Y. Synlett 2003, 1527-1529. (c) Chandrasekhar, S.; Mohapatra, S. Tetrahedron Lett. 1998, 39, 6415-6418. (d) Alcón, M.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 2967-2974. (e) Wei, Z.-Y.; Knaus, E. E. Tetrahedron 1994, 50, 5569-78. (f) Wei, Z. Y.; Knaus, E. E. J. Org. Chem. 1993, 58, 1586-8.
24. S)-Vigabatrin: (a) Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413. (b) Masson, G.; Zeghida, W.; Cividino, P.; Py, S.; Vallee, Y. Synlett 2003, 1527-1529. (c) Chandrasekhar, S.; Mohapatra, S. Tetrahedron Lett. 1998, 39, 6415-6418. (d) Alcón, M.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 2967-2974. (e) Wei, Z.-Y.; Knaus, E. E. Tetrahedron 1994, 50, 5569-78. (f) Wei, Z. Y.; Knaus, E. E. J. Org. Chem. 1993, 58, 1586-8.
25. S)-Vigabatrin: (a) Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413. (b) Masson, G.; Zeghida, W.; Cividino, P.; Py, S.; Vallee, Y. Synlett 2003, 1527-1529. (c) Chandrasekhar, S.; Mohapatra, S. Tetrahedron Lett. 1998, 39, 6415-6418. (d) Alcón, M.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 2967-2974. (e) Wei, Z.-Y.; Knaus, E. E. Tetrahedron 1994, 50, 5569-78. (f) Wei, Z. Y.; Knaus, E. E. J. Org. Chem. 1993, 58, 1586-8.
26. S)-Vigabatrin: (a) Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413. (b) Masson, G.; Zeghida, W.; Cividino, P.; Py, S.; Vallee, Y. Synlett 2003, 1527-1529. (c) Chandrasekhar, S.; Mohapatra, S. Tetrahedron Lett. 1998, 39, 6415-6418. (d) Alcón, M.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 2967-2974. (e) Wei, Z.-Y.; Knaus, E. E. Tetrahedron 1994, 50, 5569-78. (f) Wei, Z. Y.; Knaus, E. E. J. Org. Chem. 1993, 58, 1586-8.
27. S)-Vigabatrin: (a) Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413. (b) Masson, G.; Zeghida, W.; Cividino, P.; Py, S.; Vallee, Y. Synlett 2003, 1527-1529. (c) Chandrasekhar, S.; Mohapatra, S. Tetrahedron Lett. 1998, 39, 6415-6418. (d) Alcón, M.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 2967-2974. (e) Wei, Z.-Y.; Knaus, E. E. Tetrahedron 1994, 50, 5569-78. (f) Wei, Z. Y.; Knaus, E. E. J. Org. Chem. 1993, 58, 1586-8.
28. Enantioenriched quaternary, α-vinylic AA's: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano. M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
29. Enantioenriched quaternary, α-vinylic AA's: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano. M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
30. Enantioenriched quaternary, α-vinylic AA's: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano. M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
31. Enantioenriched quaternary, α-vinylic AA's: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano. M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
32. Enantioenriched quaternary, α-vinylic AA's: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano. M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
33. Enantioenriched quaternary, α-vinylic AA's: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano. M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
34. Enantioenriched quaternary, α-vinylic AA's: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano. M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
35. Enantioenriched quaternary, α-vinylic AA's: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano. M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
36. Enantioenriched quaternary, α-vinylic AA's: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano. M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
37. Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1988, 29, 99-102.
38. Larksarp, C.; Alper, H. J. Am. Chem. Soc. 1997, 119, 3709-3715.
39. Trost, B. M.; Bunt, R. C.; Lemoine, R. C.; Calkins, T. L. J. Am. Chem. Soc. 2000, 122, 5968-5976.
40. Overman uses a Pd(II) catalyst and invokes an intramolecular, aminopalladation mechanism that preserves the Pd(II) oxidation state throughout the catalytic cycle: Overman, L. O.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13.
41. Berkowitz, D. B.; Bose, M.; Choi, S. Angew. Chem., Int. Ed. 2002, 41, 1603-1607.
42. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066.
43. Schmid, R.; Foricher, J.; Cereghetti, M.; Schoenholzer, P. Helv. Chim. Acta 1991, 74, 370-389.
44. BIPHEP ligands have been utilized mostly for asymmetric Ru-mediated ketone reductions. For a leading reference, see: Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal V.; Genêt, J.-P.; Champion, N.; Dellis, P. Angew. Chem., Int. Ed. 2004, 43, 320-325.
45. For examples of Pd-mediated allylic substitutions using BIPHEP, see: (a) Sinou, D.; Rabeyrin, C.; Nguefack, C. Adv. Synth. Catal. 2003, 345, 357-363. (b) Bolm, C.; Kaufmann, D.; Gessler, S.; Harms, K. J. Organomet. Chem. 1995, 502, 47-52. (c) Barbara, P. S.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160-5170.
46. For examples of Pd-mediated allylic substitutions using BIPHEP, see: (a) Sinou, D.; Rabeyrin, C.; Nguefack, C. Adv. Synth. Catal. 2003, 345, 357-363. (b) Bolm, C.; Kaufmann, D.; Gessler, S.; Harms, K. J. Organomet. Chem. 1995, 502, 47-52. (c) Barbara, P. S.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160-5170.
47. For examples of Pd-mediated allylic substitutions using BIPHEP, see: (a) Sinou, D.; Rabeyrin, C.; Nguefack, C. Adv. Synth. Catal. 2003, 345, 357-363. (b) Bolm, C.; Kaufmann, D.; Gessler, S.; Harms, K. J. Organomet. Chem. 1995, 502, 47-52. (c) Barbara, P. S.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160-5170.
48. (a) Bricout, H.; Carpentier, J.-F.; Mortreux, A. Tetrahedron 1998, 54, 1073-1084.
49. (b) Bricout, H.; Carpentier, J.-F.; Mortreux, A. Chem. Commun. 1995, 1863-1864.
50. For evidence of π-allyl nickel intermediates, see: (c) Moberg, C. Tetrahedron Lett. 1980, 21, 4539-4542. (d) Yamamoto, T.; Ishizu, J.; Yamamoto, A. J. Am. Chem. Soc. 1981, 103, 6863-6869. (e) Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 6785-6790.
51. For evidence of π-allyl nickel intermediates, see: (c) Moberg, C. Tetrahedron Lett. 1980, 21, 4539-4542. (d) Yamamoto, T.; Ishizu, J.; Yamamoto, A. J. Am. Chem. Soc. 1981, 103, 6863-6869. (e) Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 6785-6790.
52. For evidence of π-allyl nickel intermediates, see: (c) Moberg, C. Tetrahedron Lett. 1980, 21, 4539-4542. (d) Yamamoto, T.; Ishizu, J.; Yamamoto, A. J. Am. Chem. Soc. 1981, 103, 6863-6869. (e) Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 6785-6790.
53. For examples of substrate-directed, regio- and stereoselective Ni(0)-mediated substitutions of allylic ethers with Grignard reagents, see: (f) Didiuk, M. T.; Morken, J. P.; Hoveyda, A. H. Tetrahedron 1998, 54, 1117-1130. (g) Farthing, C. N.; Kocovsky, P. J. Am. Chem. Soc. 1998, 120, 6661-6672.
54. For examples of substrate-directed, regio- and stereoselective Ni(0)-mediated substitutions of allylic ethers with Grignard reagents, see: (f) Didiuk, M. T.; Morken, J. P.; Hoveyda, A. H. Tetrahedron 1998, 54, 1117-1130. (g) Farthing, C. N.; Kocovsky, P. J. Am. Chem. Soc. 1998, 120, 6661-6672.
55. (a) Trost, B. M.; Shen, H. C.; Dong, L.; Surivet, J.-P. J. Am. Chem. Soc. 2003, 125, 9276-9277.
56. (b) Bartels, B.; García-Yebra, C.; Rominger, F.; Helmchen, G. Eur. J. Inorg. Chem. 2002, 2569-2586.
57. (c) Welter, C.; Koch, O.; Lipowsky, G.; Helmchen, G. Chem. Commun. 2004, 896-897
58. (d) Burckhardt, U.; Baumann, M.; Togni, A. Tetrahedron: Asymmetry 1997, 8, 155-159.
59. OMP = o-methoxyphenyl. TMP = 3,4,5-trimethoxyphenyl.