Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3873-3876

  Defieber, Christian ^a   Paquin, Jean François ^a   Serna, Sonia ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; BORONIC ACID DERIVATIVE; LIGAND; RHODIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; LIGAND BINDING; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 7044246039     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048240x     Document Type: Article

References (31)

1. Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508.
2. Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628.
3. For a mini review, see: Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364; Angew. Chem. 2004, 116, 3444.
4. For a mini review, see: Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364; Angew. Chem. 2004, 116, 3444.
5. For reviews involving the addition of boronic acids to acceptors using complexes derived from chiral phosphines, see: (a) Hayashi, T. Bull. Chem. Soc. Jpn. 2004, 77, 13. (b) Hayashi, T. Pure Appl. Chem. 2004, 76, 465. (c) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829. (d) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
6. For reviews involving the addition of boronic acids to acceptors using complexes derived from chiral phosphines, see: (a) Hayashi, T. Bull. Chem. Soc. Jpn. 2004, 77, 13. (b) Hayashi, T. Pure Appl. Chem. 2004, 76, 465. (c) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829. (d) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
7. For reviews involving the addition of boronic acids to acceptors using complexes derived from chiral phosphines, see: (a) Hayashi, T. Bull. Chem. Soc. Jpn. 2004, 77, 13. (b) Hayashi, T. Pure Appl. Chem. 2004, 76, 465. (c) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829. (d) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
8. For reviews involving the addition of boronic acids to acceptors using complexes derived from chiral phosphines, see: (a) Hayashi, T. Bull. Chem. Soc. Jpn. 2004, 77, 13. (b) Hayashi, T. Pure Appl. Chem. 2004, 76, 465. (c) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829. (d) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
9. Mechanistic study: Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
10. For additions of boronic acids to unsaturated ketones employing phosphine ligands, see: (a) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871; Angew. Chem. 2003, 115, 6051. (b) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 11, 1791. (c) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 7, 1040. (d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552. (e) Reetz, M.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (f) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 685. (f) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111. (g) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (i) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
11. For additions of boronic acids to unsaturated ketones employing phosphine ligands, see: (a) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871; Angew. Chem. 2003, 115, 6051. (b) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 11, 1791. (c) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 7, 1040. (d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552. (e) Reetz, M.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (f) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 685. (f) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111. (g) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (i) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
12. For additions of boronic acids to unsaturated ketones employing phosphine ligands, see: (a) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871; Angew. Chem. 2003, 115, 6051. (b) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 11, 1791. (c) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 7, 1040. (d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552. (e) Reetz, M.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (f) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 685. (f) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111. (g) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (i) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
13. For additions of boronic acids to unsaturated ketones employing phosphine ligands, see: (a) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871; Angew. Chem. 2003, 115, 6051. (b) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 11, 1791. (c) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 7, 1040. (d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552. (e) Reetz, M.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (f) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 685. (f) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111. (g) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (i) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
14. For additions of boronic acids to unsaturated ketones employing phosphine ligands, see: (a) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871; Angew. Chem. 2003, 115, 6051. (b) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 11, 1791. (c) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 7, 1040. (d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552. (e) Reetz, M.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (f) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 685. (f) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111. (g) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (i) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
15. For additions of boronic acids to unsaturated ketones employing phosphine ligands, see: (a) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871; Angew. Chem. 2003, 115, 6051. (b) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 11, 1791. (c) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 7, 1040. (d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552. (e) Reetz, M.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (f) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 685. (f) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111. (g) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (i) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
16. For additions of boronic acids to unsaturated ketones employing phosphine ligands, see: (a) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871; Angew. Chem. 2003, 115, 6051. (b) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 11, 1791. (c) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 7, 1040. (d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552. (e) Reetz, M.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (f) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 685. (f) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111. (g) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (i) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
17. For additions of boronic acids to unsaturated ketones employing phosphine ligands, see: (a) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871; Angew. Chem. 2003, 115, 6051. (b) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 11, 1791. (c) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 7, 1040. (d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552. (e) Reetz, M.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (f) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 685. (f) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111. (g) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (i) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
18. For additions of boronic acids to unsaturated ketones employing phosphine ligands, see: (a) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871; Angew. Chem. 2003, 115, 6051. (b) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 11, 1791. (c) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 7, 1040. (d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552. (e) Reetz, M.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (f) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 685. (f) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111. (g) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (i) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
19. For additions of boronic acids to unsaturated ketones employing phosphine ligands, see: (a) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem., Int. Ed. 2003, 42, 5871; Angew. Chem. 2003, 115, 6051. (b) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 11, 1791. (c) Iguchi, Y.; Itooka, R.; Miyaura, N. Synlett 2003, 7, 1040. (d) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552. (e) Reetz, M.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083. (f) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 685. (f) Duursma, A.; Hoen, R.; Schuppan, J.; Hulst, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 3111. (g) Kuriyama, M.; Nagai, K.; Yamada, K.-i.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932. (i) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
20. Meyer, O.; Becht, J.-M.; Helmchen, G. Synlett 2003, 10, 1539.
21. For additions of boronic acids to unsaturated esters employing phosphine ligands with control at both α and β carbons, see: (a) Navarre, L.; Darses, S.; Genêt, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719; Angew. Chem. 2004, 116, 737. (b) Navarre, L.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2004, 69. (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (d) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
22. For additions of boronic acids to unsaturated esters employing phosphine ligands with control at both α and β carbons, see: (a) Navarre, L.; Darses, S.; Genêt, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719; Angew. Chem. 2004, 116, 737. (b) Navarre, L.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2004, 69. (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (d) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
23. For additions of boronic acids to unsaturated esters employing phosphine ligands with control at both α and β carbons, see: (a) Navarre, L.; Darses, S.; Genêt, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719; Angew. Chem. 2004, 116, 737. (b) Navarre, L.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2004, 69. (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (d) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
24. For additions of boronic acids to unsaturated esters employing phosphine ligands with control at both α and β carbons, see: (a) Navarre, L.; Darses, S.; Genêt, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719; Angew. Chem. 2004, 116, 737. (b) Navarre, L.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2004, 69. (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (d) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
25. For additions of boronic acids to unsaturated esters employing phosphine ligands with control at both α and β carbons, see: (a) Navarre, L.; Darses, S.; Genêt, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719; Angew. Chem. 2004, 116, 737. (b) Navarre, L.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2004, 69. (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. (d) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
26. For the addition of boronic acids to amides and vinylogous amides employing phosphine ligands, see: (a) Shintani, R.; Tokunaga, N.; Doi, H.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 6240. (b) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944.
27. For the addition of boronic acids to amides and vinylogous amides employing phosphine ligands, see: (a) Shintani, R.; Tokunaga, N.; Doi, H.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 6240. (b) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944.
28. For the addition of boronic acids to amides and vinylogous amides employing phosphine ligands, see: (a) Shintani, R.; Tokunaga, N.; Doi, H.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 6240. (b) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. (c) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944.
29. As shown in Scheme 1, the final step in the synthesis of 1 furnishes the diene ligand in good yields. The conversions of 11b-e to 2-5 proceeded in considerably poorer yields (18-42%); however, these yields were unoptimized, as the ligands were shown to be inferior (Table 1).
30. (a) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 17.
31. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221.