Homochiral cyclopentane-based C1-symmetric P,P ligands C 5H8(PPh2)(PR2) from C 2-symmetric C5H8(PCl2)2

Tetrahedron Letters

Volumn 44, Issue 52, 2003, Pages 9279-9281

  Dahlenburg, Lutz ^a   Wühr, Andreas ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Chirality; Dissymmetric P2 ligands; Synthetic methods

Indexed keywords

CYCLOPENTANE; LIGAND; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL BOND; ENANTIOMER; GAS;

EID: 0344441311     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.071     Document Type: Article

References (29)

1. For chiral phosphine-phosphites in asymmetric catalysis, see e.g.: (a) Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413-4423; (b) Franciò, G.; Wittmann, K.; Leitner, W. J. Organomet. Chem. 2001, 621, 130-142; (c) Deerenberg, S.; Pàmies, O.; Diéguez, M.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 7626-7631; (d) Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Org. Chem. 2001, 66, 8364-8369; (e) Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2861-2866; (f) Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 3441-3445; (g) Diéguez, M.; Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. J. Mol. Cat. A: Chem. 2002, 185, 11-16.
2. For chiral phosphine-phosphites in asymmetric catalysis, see e.g.: (a) Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413-4423; (b) Franciò, G.; Wittmann, K.; Leitner, W. J. Organomet. Chem. 2001, 621, 130-142; (c) Deerenberg, S.; Pàmies, O.; Diéguez, M.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 7626-7631; (d) Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Org. Chem. 2001, 66, 8364-8369; (e) Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2861-2866; (f) Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 3441-3445; (g) Diéguez, M.; Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. J. Mol. Cat. A: Chem. 2002, 185, 11-16.
3. For chiral phosphine-phosphites in asymmetric catalysis, see e.g.: (a) Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413-4423; (b) Franciò, G.; Wittmann, K.; Leitner, W. J. Organomet. Chem. 2001, 621, 130-142; (c) Deerenberg, S.; Pàmies, O.; Diéguez, M.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 7626-7631; (d) Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Org. Chem. 2001, 66, 8364-8369; (e) Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2861-2866; (f) Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 3441-3445; (g) Diéguez, M.; Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. J. Mol. Cat. A: Chem. 2002, 185, 11-16.
4. For chiral phosphine-phosphites in asymmetric catalysis, see e.g.: (a) Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413-4423; (b) Franciò, G.; Wittmann, K.; Leitner, W. J. Organomet. Chem. 2001, 621, 130-142; (c) Deerenberg, S.; Pàmies, O.; Diéguez, M.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 7626-7631; (d) Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Org. Chem. 2001, 66, 8364-8369; (e) Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2861-2866; (f) Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 3441-3445; (g) Diéguez, M.; Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. J. Mol. Cat. A: Chem. 2002, 185, 11-16.
5. For chiral phosphine-phosphites in asymmetric catalysis, see e.g.: (a) Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413-4423; (b) Franciò, G.; Wittmann, K.; Leitner, W. J. Organomet. Chem. 2001, 621, 130-142; (c) Deerenberg, S.; Pàmies, O.; Diéguez, M.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 7626-7631; (d) Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Org. Chem. 2001, 66, 8364-8369; (e) Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2861-2866; (f) Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 3441-3445; (g) Diéguez, M.; Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. J. Mol. Cat. A: Chem. 2002, 185, 11-16.
6. For chiral phosphine-phosphites in asymmetric catalysis, see e.g.: (a) Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413-4423; (b) Franciò, G.; Wittmann, K.; Leitner, W. J. Organomet. Chem. 2001, 621, 130-142; (c) Deerenberg, S.; Pàmies, O.; Diéguez, M.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 7626-7631; (d) Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Org. Chem. 2001, 66, 8364-8369; (e) Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2861-2866; (f) Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 3441-3445; (g) Diéguez, M.; Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. J. Mol. Cat. A: Chem. 2002, 185, 11-16.
7. For chiral phosphine-phosphites in asymmetric catalysis, see e.g.: (a) Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413-4423; (b) Franciò, G.; Wittmann, K.; Leitner, W. J. Organomet. Chem. 2001, 621, 130-142; (c) Deerenberg, S.; Pàmies, O.; Diéguez, M.; Claver, C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Org. Chem. 2001, 66, 7626-7631; (d) Pàmies, O.; Diéguez, M.; Net, G.; Ruiz, A.; Claver, C. J. Org. Chem. 2001, 66, 8364-8369; (e) Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2861-2866; (f) Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 3441-3445; (g) Diéguez, M.; Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. J. Mol. Cat. A: Chem. 2002, 185, 11-16.
8. Chiral phosphite-phosphoroamidites: (a) Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2827-2834; (b) Diéguez, M.; Ruiz, A.; Claver, C. Chem. Commun. 2001, 2702-2703.
9. Chiral phosphite-phosphoroamidites: (a) Diéguez, M.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 2827-2834; (b) Diéguez, M.; Ruiz, A.; Claver, C. Chem. Commun. 2001, 2702-2703.
10. 2 ligands without additional stereogenic centers in the donor groups, see: (a) Kapoor, P. N.; Pathak, D.; Gaur, G.; Kutty, M. J. Organomet. Chem. 1984, 276, 167-170; (b) Brunner, H.; Stumpf, A. J. Organomet. Chem. 1993, 459, 139-144; (c) Casey, C. P.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1999, 121, 63-70; (d) Carraz, C.-A.; Ditzel, E. J.; Orpen, A. G.; Ellis, D. D.; Pringle, P. G.; Sunley, G. J. Chem. Commun. 2000, 1277-1278; (e) Hegedüs, C.; Madarász, J.; Gulyás, H.; Szöllosy, A.; Bakos, J. Tetrahedron: Asymmetry 2001, 12, 2867-2873.
11. 2 ligands without additional stereogenic centers in the donor groups, see: (a) Kapoor, P. N.; Pathak, D.; Gaur, G.; Kutty, M. J. Organomet. Chem. 1984, 276, 167-170; (b) Brunner, H.; Stumpf, A. J. Organomet. Chem. 1993, 459, 139-144; (c) Casey, C. P.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1999, 121, 63-70; (d) Carraz, C.-A.; Ditzel, E. J.; Orpen, A. G.; Ellis, D. D.; Pringle, P. G.; Sunley, G. J. Chem. Commun. 2000, 1277-1278; (e) Hegedüs, C.; Madarász, J.; Gulyás, H.; Szöllosy, A.; Bakos, J. Tetrahedron: Asymmetry 2001, 12, 2867-2873.
12. 2 ligands without additional stereogenic centers in the donor groups, see: (a) Kapoor, P. N.; Pathak, D.; Gaur, G.; Kutty, M. J. Organomet. Chem. 1984, 276, 167-170; (b) Brunner, H.; Stumpf, A. J. Organomet. Chem. 1993, 459, 139-144; (c) Casey, C. P.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1999, 121, 63-70; (d) Carraz, C.-A.; Ditzel, E. J.; Orpen, A. G.; Ellis, D. D.; Pringle, P. G.; Sunley, G. J. Chem. Commun. 2000, 1277-1278; (e) Hegedüs, C.; Madarász, J.; Gulyás, H.; Szöllosy, A.; Bakos, J. Tetrahedron: Asymmetry 2001, 12, 2867-2873.
13. 2 ligands without additional stereogenic centers in the donor groups, see: (a) Kapoor, P. N.; Pathak, D.; Gaur, G.; Kutty, M. J. Organomet. Chem. 1984, 276, 167-170; (b) Brunner, H.; Stumpf, A. J. Organomet. Chem. 1993, 459, 139-144; (c) Casey, C. P.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1999, 121, 63-70; (d) Carraz, C.-A.; Ditzel, E. J.; Orpen, A. G.; Ellis, D. D.; Pringle, P. G.; Sunley, G. J. Chem. Commun. 2000, 1277-1278; (e) Hegedüs, C.; Madarász, J.; Gulyás, H.; Szöllosy, A.; Bakos, J. Tetrahedron: Asymmetry 2001, 12, 2867-2873.
14. 2 ligands without additional stereogenic centers in the donor groups, see: (a) Kapoor, P. N.; Pathak, D.; Gaur, G.; Kutty, M. J. Organomet. Chem. 1984, 276, 167-170; (b) Brunner, H.; Stumpf, A. J. Organomet. Chem. 1993, 459, 139-144; (c) Casey, C. P.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1999, 121, 63-70; (d) Carraz, C.-A.; Ditzel, E. J.; Orpen, A. G.; Ellis, D. D.; Pringle, P. G.; Sunley, G. J. Chem. Commun. 2000, 1277-1278; (e) Hegedüs, C.; Madarász, J.; Gulyás, H.; Szöllosy, A.; Bakos, J. Tetrahedron: Asymmetry 2001, 12, 2867-2873.
15. Dissymmetric P-chirogenic bisphosphines: (a) Ohashi, A.; Imamoto, T. Org. Lett. 2001, 3, 373-375; (b) Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099-1101; (c) Ohashi, A.; Kikuchi, S.; Yasutake, A.; Imamoto, T. Eur. J. Org. Chem. 2002, 2535-2546; (d) Ohashi, A. Chirality 2002, 14, 573-577.
16. Dissymmetric P-chirogenic bisphosphines: (a) Ohashi, A.; Imamoto, T. Org. Lett. 2001, 3, 373-375; (b) Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099-1101; (c) Ohashi, A.; Kikuchi, S.; Yasutake, A.; Imamoto, T. Eur. J. Org. Chem. 2002, 2535-2546; (d) Ohashi, A. Chirality 2002, 14, 573-577.
17. Dissymmetric P-chirogenic bisphosphines: (a) Ohashi, A.; Imamoto, T. Org. Lett. 2001, 3, 373-375; (b) Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099-1101; (c) Ohashi, A.; Kikuchi, S.; Yasutake, A.; Imamoto, T. Eur. J. Org. Chem. 2002, 2535-2546; (d) Ohashi, A. Chirality 2002, 14, 573-577.
18. Dissymmetric P-chirogenic bisphosphines: (a) Ohashi, A.; Imamoto, T. Org. Lett. 2001, 3, 373-375; (b) Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099-1101; (c) Ohashi, A.; Kikuchi, S.; Yasutake, A.; Imamoto, T. Eur. J. Org. Chem. 2002, 2535-2546; (d) Ohashi, A. Chirality 2002, 14, 573-577.
19. Racemic 1 : Allen D.L., Gibson V.C., Green M.L.H., Skinner J.F., Bashkin J., Grebenik P.D. J. Chem. Soc., Chem. Commun. 1983;895-896.
20. Enantiomerically pure 1 : (a) Dahlenburg, L.; Kaunert, A. Eur. J. Inorg. Chem. 1998, 885-887; (b) Dahlenburg, L. Ger. Offen. DE 19732805 A1, 1999, 1-29 [Chem. Abstr. 1999, 130, 168481]; (c) Mertel, S. Dissertation, Universität Erlangen-Nürnberg, 2001; (d) Brunner, H.; Stefaniak, S.; Zabel, M. Synthesis 1999, 1776-1784; (e) Brunner, H.; Stefaniak, S.; Zabel, M. Synthesis 2000, 478 [Erratum].
21. Enantiomerically pure 1 : (a) Dahlenburg, L.; Kaunert, A. Eur. J. Inorg. Chem. 1998, 885-887; (b) Dahlenburg, L. Ger. Offen. DE 19732805 A1, 1999, 1-29 [Chem. Abstr. 1999, 130, 168481]; (c) Mertel, S. Dissertation, Universität Erlangen-Nürnberg, 2001; (d) Brunner, H.; Stefaniak, S.; Zabel, M. Synthesis 1999, 1776-1784; (e) Brunner, H.; Stefaniak, S.; Zabel, M. Synthesis 2000, 478 [Erratum].
22. Enantiomerically pure 1 : (a) Dahlenburg, L.; Kaunert, A. Eur. J. Inorg. Chem. 1998, 885-887; (b) Dahlenburg, L. Ger. Offen. DE 19732805 A1, 1999, 1-29 [Chem. Abstr. 1999, 130, 168481]; (c) Mertel, S. Dissertation, Universität Erlangen-Nürnberg, 2001; (d) Brunner, H.; Stefaniak, S.; Zabel, M. Synthesis 1999, 1776-1784; (e) Brunner, H.; Stefaniak, S.; Zabel, M. Synthesis 2000, 478 [Erratum].
23. Enantiomerically pure 1 : (a) Dahlenburg, L.; Kaunert, A. Eur. J. Inorg. Chem. 1998, 885-887; (b) Dahlenburg, L. Ger. Offen. DE 19732805 A1, 1999, 1-29 [Chem. Abstr. 1999, 130, 168481]; (c) Mertel, S. Dissertation, Universität Erlangen-Nürnberg, 2001; (d) Brunner, H.; Stefaniak, S.; Zabel, M. Synthesis 1999, 1776-1784; (e) Brunner, H.; Stefaniak, S.; Zabel, M. Synthesis 2000, 478 [Erratum].
24. Enantiomerically pure 1 : (a) Dahlenburg, L.; Kaunert, A. Eur. J. Inorg. Chem. 1998, 885-887; (b) Dahlenburg, L. Ger. Offen. DE 19732805 A1, 1999, 1-29 [Chem. Abstr. 1999, 130, 168481]; (c) Mertel, S. Dissertation, Universität Erlangen-Nürnberg, 2001; (d) Brunner, H.; Stefaniak, S.; Zabel, M. Synthesis 1999, 1776-1784; (e) Brunner, H.; Stefaniak, S.; Zabel, M. Synthesis 2000, 478 [Erratum].
25. 3, 20°C); (1R,2R)-2 : +78 (589 nm), +85 (578 nm), +95 (546 nm), +176 (436 nm), +299 (365 nm). (1S,2S)-2 : -96 (589 nm), -107 (578 nm), -124 (546 nm), -220 (436 nm), -355 (365 nm).
26. 3, 20°C); (1R,2R)-3 : +164 (589 nm), +171 (578 nm), +199 (546 nm), +383 (436 nm), +724 (365 nm). (1S,2S)-3 : -130 (589 nm), -138 (578 nm), -159 (546 nm), -307 (436 nm), -682 (365 nm).
27. 3, 20°C); (1R,2R)-4 : -16 (589 nm), -17 (578 nm), -19 (546 nm), -31 (436 nm), +45 (365 nm). (1S,2S)-4 : +15 (589 nm), +17 (578 nm), +18 (546 nm), +30 (436 nm), -45 (365 nm).
28. 3, 20°C); (1R,2R)-5 : +6 (589 nm), +7 (578 nm), +8 (546 nm), +20 (436 nm), +44 (365 nm). (1S,2S)-5 : -9 (589 nm), -10 (578 nm), -12 (546 nm), -26 (436 nm), -57 (365 nm).
29. Dahlenburg L., Becker C., Höck J., Mertel S. J. Organomet. Chem. 564:1998;155(166.