Highly flexible synthetic routes to functionalized phospholanes from carbohydrates

Journal of Organic Chemistry

Volumn 65, Issue 3, 2000, Pages 900-906

  Yan, Yuan Yong ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; LIGAND; LITHIUM; MANNITOL; PHOSPHINE DERIVATIVE; REAGENT;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; SYNTHESIS;

EID: 0033950906     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991762j     Document Type: Article

References (70)

1. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
2. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
3. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
4. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
5. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
6. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
7. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
8. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
9. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
10. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
11. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
12. For some early representative examples, see: (a) Kawabata, Y.; Tanaka, M.; Ogata, I. Chem. Lett. 1970, 1213. (b) Jackson, R.; Thompson, D. J. J. Organomet. Chem. 1978, 159, C29. (c) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 1635. (d) Selke, R. React. Kinetic. Catal. Lett. 1979, 10, 135. (e) Nakamura, Y.; Saito, S.; Morita, Y. Chem. Lett. 1980, 7. ( f) Johnson, T. H.; Rangarajan, G. J. Org. Chem. 1980, 45, 62. (g) Brunner, H.; Pieronczyk, W. J. Chem. Res., Synop. 1980, 76. (h) Yamada, M.; Yamashita, M.; Inokawa, S. Carbohydr. Res. 1981, 95, C9. (i) Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. (j) Brown, J. M.; Cook, S. J. Tetrahedron 1986, 42, 5105. For recent reviews, see: (k) Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1997, 983. (l) RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A. Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions. In Advances in Catalytic Processes; Doyle, M., Ed.; JAI Press: Greenwich, CT, 1998; pp 1-41.
13. (a) Ni-catalyzed hydrocyanation: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. See also: Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197 and references therein. (c) Hydroformylation: RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. (d) Hydrovinylation: Park, H.; RajanBabu, T. V. Unpublished results. (e) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601. See also: Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
14. (a) Ni-catalyzed hydrocyanation: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. See also: Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197 and references therein. (c) Hydroformylation: RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. (d) Hydrovinylation: Park, H.; RajanBabu, T. V. Unpublished results. (e) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601. See also: Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
15. (a) Ni-catalyzed hydrocyanation: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. See also: Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197 and references therein. (c) Hydroformylation: RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. (d) Hydrovinylation: Park, H.; RajanBabu, T. V. Unpublished results. (e) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601. See also: Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
16. (a) Ni-catalyzed hydrocyanation: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. See also: Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197 and references therein. (c) Hydroformylation: RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. (d) Hydrovinylation: Park, H.; RajanBabu, T. V. Unpublished results. (e) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601. See also: Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
17. (a) Ni-catalyzed hydrocyanation: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. See also: Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197 and references therein. (c) Hydroformylation: RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. (d) Hydrovinylation: Park, H.; RajanBabu, T. V. Unpublished results. (e) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601. See also: Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
18. (a) Ni-catalyzed hydrocyanation: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. See also: Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197 and references therein. (c) Hydroformylation: RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. (d) Hydrovinylation: Park, H.; RajanBabu, T. V. Unpublished results. (e) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601. See also: Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
19. (a) Ni-catalyzed hydrocyanation: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. See also: Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197 and references therein. (c) Hydroformylation: RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. (d) Hydrovinylation: Park, H.; RajanBabu, T. V. Unpublished results. (e) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601. See also: Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
20. (a) Ni-catalyzed hydrocyanation: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. See also: Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197 and references therein. (c) Hydroformylation: RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. (d) Hydrovinylation: Park, H.; RajanBabu, T. V. Unpublished results. (e) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601. See also: Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
21. (a) Ni-catalyzed hydrocyanation: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869. (b) Rh-catalyzed hydrogenations: RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. See also: Kumar, A.; Oehme, G.; Roque, J. P.; Schwarze, M.; Selke, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2197 and references therein. (c) Hydroformylation: RajanBabu, T. V.; Ayers, T. A. Tetrahedron Lett. 1994, 35, 4295. (d) Hydrovinylation: Park, H.; RajanBabu, T. V. Unpublished results. (e) Pd-catalyzed allylation: Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745. Clyne, D.; Mermet-Bouvier, Y. C.; Nomura, N.; RajanBabu, T. V. J. Org. Chem. 1999, 64, 7601. See also: Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
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36. An outstanding example of this is the sulfonated triphenylphosphine, BINAP, and their analogues. See refs 4 and 5. See also: (a) Nagel, U.; Kinzel, E. Chem. Ber. 1986, 119, 1731. (b) Tóth, I.; Hanson, B. E. Tetrahedron Asymmetry 1990, 1, 895. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303.
37. An outstanding example of this is the sulfonated triphenylphosphine, BINAP, and their analogues. See refs 4 and 5. See also: (a) Nagel, U.; Kinzel, E. Chem. Ber. 1986, 119, 1731. (b) Tóth, I.; Hanson, B. E. Tetrahedron Asymmetry 1990, 1, 895. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303.
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45. While our studies were in progress, a number of reports dealing with the synthesis of functionalized bisphospholanes have appeared. (a) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031. (b) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261. (c) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701. (d) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. The earliest report in this area, which appeared in 1992, has received no mention in subsequent papers: Hitchcock, P. B.; Lappert, M. F. Yin, P. J. Chem. Soc., Chem. Commun. 1992, 1598.
46. While our studies were in progress, a number of reports dealing with the synthesis of functionalized bisphospholanes have appeared. (a) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031. (b) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261. (c) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701. (d) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. The earliest report in this area, which appeared in 1992, has received no mention in subsequent papers: Hitchcock, P. B.; Lappert, M. F. Yin, P. J. Chem. Soc., Chem. Commun. 1992, 1598.
47. While our studies were in progress, a number of reports dealing with the synthesis of functionalized bisphospholanes have appeared. (a) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031. (b) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261. (c) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701. (d) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. The earliest report in this area, which appeared in 1992, has received no mention in subsequent papers: Hitchcock, P. B.; Lappert, M. F. Yin, P. J. Chem. Soc., Chem. Commun. 1992, 1598.
48. While our studies were in progress, a number of reports dealing with the synthesis of functionalized bisphospholanes have appeared. (a) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031. (b) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261. (c) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701. (d) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. The earliest report in this area, which appeared in 1992, has received no mention in subsequent papers: Hitchcock, P. B.; Lappert, M. F. Yin, P. J. Chem. Soc., Chem. Commun. 1992, 1598.
49. While our studies were in progress, a number of reports dealing with the synthesis of functionalized bisphospholanes have appeared. (a) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031. (b) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261. (c) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701. (d) Holz, J.; Heller, D.; Stürmer, R.; Börner, A. Tetrahedron Lett. 1999, 40, 7059. The earliest report in this area, which appeared in 1992, has received no mention in subsequent papers: Hitchcock, P. B.; Lappert, M. F. Yin, P. J. Chem. Soc., Chem. Commun. 1992, 1598.
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63. For typical examples, see: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523. (c) Williams, J. M. J. Synlett 1996, 705. (d) Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35. (e) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. For recent examples, see: (f) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (g) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
64. For typical examples, see: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523. (c) Williams, J. M. J. Synlett 1996, 705. (d) Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35. (e) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. For recent examples, see: (f) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (g) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
65. For typical examples, see: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523. (c) Williams, J. M. J. Synlett 1996, 705. (d) Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35. (e) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. For recent examples, see: (f) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (g) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
66. For typical examples, see: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523. (c) Williams, J. M. J. Synlett 1996, 705. (d) Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35. (e) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. For recent examples, see: (f) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (g) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
67. For typical examples, see: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523. (c) Williams, J. M. J. Synlett 1996, 705. (d) Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35. (e) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. For recent examples, see: (f) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (g) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
68. For typical examples, see: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523. (c) Williams, J. M. J. Synlett 1996, 705. (d) Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35. (e) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. For recent examples, see: (f) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (g) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
69. For typical examples, see: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523. (c) Williams, J. M. J. Synlett 1996, 705. (d) Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35. (e) Schnyder, A.; Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 931. For recent examples, see: (f) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (g) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994.
70. Note added in proof: Applications of these ligands for a prototypical Pd(0)-catalyzed allylation (yields up to 99% and ee's >99% in selected cases) have been reported. Yan, Y.; RajanBabu, T. V. Org. Lett. 2000, 2, 199.