The application of Pd-complexes of trans-2,5-dialkylpyrrolidinyl- benzyldiphenylphosphines to enantioselective allylic alkylation

Tetrahedron Asymmetry

Volumn 9, Issue 24, 1998, Pages 4301-4305

  Cahill, John P ^a   Guiry, Patrick J ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; SOLVENT;

ALKYLATION; ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 0032564706     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00425-X     Document Type: Article

References (43)

1. Reviews: (a) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994, pp. 82-85. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993, p. 325 Heumann, A. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds; Wiley VCH: Weinheim, 1998, pp. 251-259. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395.
2. Reviews: (a) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994, pp. 82-85. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993, p. 325 Heumann, A. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds; Wiley VCH: Weinheim, 1998, pp. 251-259. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395.
3. Reviews: (a) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994, pp. 82-85. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993, p. 325 Heumann, A. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds; Wiley VCH: Weinheim, 1998, pp. 251-259. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395.
4. Reviews: (a) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994, pp. 82-85. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993, p. 325 Heumann, A. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds; Wiley VCH: Weinheim, 1998, pp. 251-259. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395.
5. Reviews: (a) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994, pp. 82-85. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993, p. 325 Heumann, A. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds; Wiley VCH: Weinheim, 1998, pp. 251-259. Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (e) Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395.
6. Selected recent diphosphine examples: (a) Trost, B. M.; van Dranken, D. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 228. (b) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, F. E., Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (e) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (f) Brencley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809. (g) Nettekoven, U.; Widhal, M.; Kamer, P. C. J.; van Leeuwen, P. W N. M. Tetrahedron: Asymmetry 1997, 8, 3185.
7. Selected recent diphosphine examples: (a) Trost, B. M.; van Dranken, D. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 228. (b) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, F. E., Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (e) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (f) Brencley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809. (g) Nettekoven, U.; Widhal, M.; Kamer, P. C. J.; van Leeuwen, P. W N. M. Tetrahedron: Asymmetry 1997, 8, 3185.
8. Selected recent diphosphine examples: (a) Trost, B. M.; van Dranken, D. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 228. (b) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, F. E., Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (e) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (f) Brencley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809. (g) Nettekoven, U.; Widhal, M.; Kamer, P. C. J.; van Leeuwen, P. W N. M. Tetrahedron: Asymmetry 1997, 8, 3185.
9. Selected recent diphosphine examples: (a) Trost, B. M.; van Dranken, D. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 228. (b) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, F. E., Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (e) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (f) Brencley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809. (g) Nettekoven, U.; Widhal, M.; Kamer, P. C. J.; van Leeuwen, P. W N. M. Tetrahedron: Asymmetry 1997, 8, 3185.
10. Selected recent diphosphine examples: (a) Trost, B. M.; van Dranken, D. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 228. (b) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, F. E., Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (e) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (f) Brencley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809. (g) Nettekoven, U.; Widhal, M.; Kamer, P. C. J.; van Leeuwen, P. W N. M. Tetrahedron: Asymmetry 1997, 8, 3185.
11. Selected recent diphosphine examples: (a) Trost, B. M.; van Dranken, D. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 228. (b) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, F. E., Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (e) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (f) Brencley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809. (g) Nettekoven, U.; Widhal, M.; Kamer, P. C. J.; van Leeuwen, P. W N. M. Tetrahedron: Asymmetry 1997, 8, 3185.
12. Selected recent diphosphine examples: (a) Trost, B. M.; van Dranken, D. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 228. (b) Yamazaki, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1993, 4, 2287. Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, F. E., Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. (e) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 51. (f) Brencley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809. (g) Nettekoven, U.; Widhal, M.; Kamer, P. C. J.; van Leeuwen, P. W N. M. Tetrahedron: Asymmetry 1997, 8, 3185.
13. (h) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179.
14. Selected recent dinitrogen examples: (a) Leutenneger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135. Tanner, D.; Andersson, P. G.; Harden, A.; Norrby, P.-O. Chem. Eur. J. 1995, 1, 12. Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (e) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571.
15. Selected recent dinitrogen examples: (a) Leutenneger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135. Tanner, D.; Andersson, P. G.; Harden, A.; Norrby, P.-O. Chem. Eur. J. 1995, 1, 12. Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (e) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571.
16. Selected recent dinitrogen examples: (a) Leutenneger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135. Tanner, D.; Andersson, P. G.; Harden, A.; Norrby, P.-O. Chem. Eur. J. 1995, 1, 12. Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (e) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571.
17. Selected recent dinitrogen examples: (a) Leutenneger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135. Tanner, D.; Andersson, P. G.; Harden, A.; Norrby, P.-O. Chem. Eur. J. 1995, 1, 12. Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (e) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571.
18. Selected recent dinitrogen examples: (a) Leutenneger, U.; Umbricht, G.; Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135. Tanner, D.; Andersson, P. G.; Harden, A.; Norrby, P.-O. Chem. Eur. J. 1995, 1, 12. Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (e) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571.
19. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
20. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
21. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
22. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
23. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
24. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
25. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
26. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
27. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
28. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
29. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
30. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
31. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
32. Selected recent phosphorus-nitrogen examples: (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689. (e) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493. (f) Togni, A.; Bruckhardt; Gramlich, V.; Progosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031. (g) Chelucci, G.; Cabras, M. A.; Botteghi, C.; Basoli, A.; Marchetti, M. Tetrahedron: Asymmetry 1996, 7, 885. (h) Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213. Zhang, W.; Toshikazu, H.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. (j) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (k) Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (n) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741.
33. Selected recent sulfur-nitrogen examples: (a) Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1 1994, 2065-2072. (b) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965. Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783. Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337. (e) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753.
34. Selected recent sulfur-nitrogen examples: (a) Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1 1994, 2065-2072. (b) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965. Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783. Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337. (e) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753.
35. Selected recent sulfur-nitrogen examples: (a) Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1 1994, 2065-2072. (b) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965. Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783. Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337. (e) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753.
36. Selected recent sulfur-nitrogen examples: (a) Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1 1994, 2065-2072. (b) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965. Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783. Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337. (e) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753.
37. Selected recent sulfur-nitrogen examples: (a) Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J. J. Chem. Soc., Perkin Trans. 1 1994, 2065-2072. (b) Chelucci, G.; Cabras, M. A. Tetrahedron: Asymmetry 1996, 7, 965. Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783. Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 2337. (e) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753.
38. Cahill, J. P.; Bohnen, F.; Goddard, R.; Krüger, C.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 3831.
39. Cahill, J. P.; Lightfoot, A. P.; Goddard, R.; Rust, J.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4307.
40. Guiry, P. J.; Hennessy, A. J.; Cahill, J. P. Topics in Catalysis 1997, 4, 311-326.
41. Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2108.
42. 4.
43. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143.