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Volumn 68, Issue 9, 2003, Pages 3679-3686

1-Phosphino-2-sulfenylferrocenes as planar chiral ligands in enantioselective palladium-catalyzed allylic substitutions

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY;

EID: 0037414501     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0340657     Document Type: Article
Times cited : (130)

References (83)
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    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
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    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 965-966
    • Chelucci, G.1    Cabras, M.A.2
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    • 1542745046 scopus 로고    scopus 로고
    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (1997) Synlett , pp. 783-785
    • Morimoto, T.1    Tachibana, K.2    Achiwa, K.3
  • 9
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    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (1997) Organometallics , vol.16 , pp. 579-590
    • Albinati, A.1    Eckert, J.2    Pregosin, P.3    Rüegger, H.4    Salzmann, R.5    Stössel, C.6
  • 10
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    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2337-2346
    • Chesney, A.1    Bryce, M.R.2    Chubb, R.W.J.3    Batsanov, A.S.4    Howard, J.A.K.5
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    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
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    • Boog-Wick, K.1    Pregosin, P.2    Trabesinger, G.3
  • 12
    • 0032556757 scopus 로고    scopus 로고
    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (1998) Chem. Commun. , pp. 2765-2766
    • You, S.-L.1    Zhou, Y.-G.2    Hou, X.-L.3    Dai, L.-X.4
  • 13
    • 0000253117 scopus 로고    scopus 로고
    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (1998) J. Org. Chem. , vol.63 , pp. 5533-5540
    • Koning, B.1    Meetsma, A.2    Kellogg, R.M.3
  • 14
    • 0000918702 scopus 로고    scopus 로고
    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (1998) Organometallics , vol.17 , pp. 4976-4982
    • Hauptman, E.1    Shapiro, R.2    Marshall, W.3
  • 15
    • 0033615516 scopus 로고    scopus 로고
    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (1999) J. Org. Chem. , vol.64 , pp. 8256-8262
    • Adams, H.1    Anderson, J.C.2    Cubbon, R.3    James, D.S.4    Mathias, J.P.5
  • 16
    • 0032769120 scopus 로고    scopus 로고
    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (1999) Synlett , pp. 1319-1321
    • Imai, Y.1    Zhang, W.2    Kida, T.3    Nakatsuji, Y.4    Ikeda, I.5
  • 17
    • 0034647340 scopus 로고    scopus 로고
    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (2000) J. Org. Chem. , vol.65 , pp. 4227-4240
    • Saitoh, A.1    Achiwa, K.2    Tanaka, K.3    Morimoto, T.4
  • 18
    • 0034972758 scopus 로고    scopus 로고
    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (2001) Synlett , pp. 923-926
    • Karlström, A.S.E.1    Huerta, F.F.2    Meuzelaar, G.J.3    Bäckwall, J.-E.4
  • 19
    • 0001001589 scopus 로고    scopus 로고
    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 1469-1474
    • Jansat, S.1    Gomez, M.2    Muller, G.3    Dieguez, M.4    Aghmiz, A.5    Claver, C.6    Masdeu-Bulto, A.M.7    Flores-Santos, L.8    Martin, E.9    Maestro, M.A.10    Mahia, J.11
  • 20
    • 0035966231 scopus 로고    scopus 로고
    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
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    • Pàmies, O.1    Van Strijdonck, G.P.F.2    Diéguez, M.3    Deerenberg, S.4    Net, G.5    Ruiz, A.6    Claver, C.7    Kamer, P.C.J.8    Van Leeuwen, P.W.N.M.9
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    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (2002) J. Org. Chem. , vol.67 , pp. 5011-5014
    • Nakano, H.1    Suzuki, Y.2    Kabuto, C.3    Fujita, R.4    Hongo, H.5
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    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
    • (2002) J. Org. Chem. , vol.67 , pp. 4684-4695
    • You, S.-L.1    Hou, X.-L.2    Dai, L.-X.3    Yu, Y.-H.4    Xia, W.5
  • 23
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    • For some recent publications on chiral thioethers as ligands in palladium chemistry, see: (a) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793-7796. (b) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895-1898. (c) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965-966. (d) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783-785. (e) Albinati, A.; Eckert, J.; Pregosin, P.; Rüegger, H.; Salzmann, R.; Stössel, C. Organometallics 1997, 16, 579-590. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337-2346. (g) Boog-Wick, K.; Pregosin, P.; Trabesinger, G. Organometallics 1998, 17, 3254-3264. (h) You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766. (i) Koning, B.; Meetsma, A.; Kellogg, R. M. J. Org. Chem. 1998, 63, 5533-5540. (j) Hauptman, E.; Shapiro, R.; Marshall, W. Organometallics 1998, 17, 4976-4982. (k) Adams, H.; Anderson, J. C.; Cubbon, R.; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256-8262. (l) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321. (m) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240. (n) Karlström, A. S. E.; Huerta, F. F.; Meuzelaar, G. J.; Bäckwall, J.-E. Synlett 2001, 923-926. (o) Jansat, S.; Gomez, M.; Muller, G.; Dieguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bulto, A. M.; Flores-Santos, L.; Martin, E.; Maestro, M. A.; Mahia, J. Tetrahedron: Asymmetry 2001, 12, 1469-1474. (p) Pàmies, O.; van Strijdonck, G. P. F.; Diéguez, M.; Deerenberg, S.; Net, G.; Ruiz, A.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 8867. (q) Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011-5014. (r) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695. (s) Page, P. C. B.; Heaney, H.; Reignier, S.; Rassias, G. A. Synlett 2003, 22-28.
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    • Similar enantioselectivities were observed using THF as solvent, but the reactivity was slower.
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    • A similar trend has been described for the case of the P,S-bidentate ligands III (see ref 7).
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    • note
    • 2 have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-185296. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (e-mail: deposit@ ccdc.cam.ac.uk).
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    • 3OD), indicative of the greater π-accepting ability of the phosphine as compared to the thioether.
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    • Although compound 4 was previously described by us (see ref 12), an improved procedure has been achieved.


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