Synthesis and reactions of optically active secondary dialkylphosphine- boranes

Journal of Organic Chemistry

Volumn 65, Issue 6, 2000, Pages 1877-1880

  Miura, Tomoya ^a   Yamada, Hironari ^a   Kikuchi, Shin Ichi ^a   Imamoto, Tsuneo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; OPTICAL ROTATION; SYNTHESIS;

EID: 0034708602     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991460h     Document Type: Article

References (57)

1. For recent representative reviews on asymmetric catalysis, see: (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis; VCH publishers: Wheinheim, 1993. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994.
2. For recent representative reviews on asymmetric catalysis, see: (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis; VCH publishers: Wheinheim, 1993. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994.
3. For an excellent review of the preparation of P-chirogenic phosphines, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For phosphine-borane reviews, see: (b) Imamoto, T. Pure Appl. Chem. 1993, 65, 655. (c) Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391-1415. (d) Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197-1248. (e) Imamoto, T. Yuki Gosei Kagaku Kyokaishi. 1998, 56, 511-520.
4. For an excellent review of the preparation of P-chirogenic phosphines, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For phosphine-borane reviews, see: (b) Imamoto, T. Pure Appl. Chem. 1993, 65, 655. (c) Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391-1415. (d) Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197-1248. (e) Imamoto, T. Yuki Gosei Kagaku Kyokaishi. 1998, 56, 511-520.
5. For an excellent review of the preparation of P-chirogenic phosphines, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For phosphine-borane reviews, see: (b) Imamoto, T. Pure Appl. Chem. 1993, 65, 655. (c) Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391-1415. (d) Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197-1248. (e) Imamoto, T. Yuki Gosei Kagaku Kyokaishi. 1998, 56, 511-520.
6. For an excellent review of the preparation of P-chirogenic phosphines, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For phosphine-borane reviews, see: (b) Imamoto, T. Pure Appl. Chem. 1993, 65, 655. (c) Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391-1415. (d) Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197-1248. (e) Imamoto, T. Yuki Gosei Kagaku Kyokaishi. 1998, 56, 511-520.
7. For an excellent review of the preparation of P-chirogenic phosphines, see: (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For phosphine-borane reviews, see: (b) Imamoto, T. Pure Appl. Chem. 1993, 65, 655. (c) Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391-1415. (d) Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197-1248. (e) Imamoto, T. Yuki Gosei Kagaku Kyokaishi. 1998, 56, 511-520.
8. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
9. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693-694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
10. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
11. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
12. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
13. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
14. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
15. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
16. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
17. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
18. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
19. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877-882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
20. For recent reports of new P-chirogenic phosphines, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271-8274. (b) Airey, A. L.; Swiegers, G. F.; Willis, A. C.; Wild, S. B. J. Chem. Soc., Chem. Commun. 1995, 693- 694. (c) Bianchini, C.; Cicchi, S.; Peruzzini, M.; Pietrusiewicz, K. M.; Brandi, A. J. Chem. Soc., Chem. Commun. 1995, 833-834. (d) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809-2812. (e) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365-1369. (f) Yang, H.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 2089-2095. (g) Hamada, Y.; Matsuura, F.; Oku, M.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1997, 38, 8961-8964. (h) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. (i) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996-4004. (j) Carmichael, D.; Doucet, H.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1999, 261-262. (k) Miura, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 4833-4836. (l) Tsuruta, H.; Imamoto, T. Tetrahedron: Asymmetry 1999, 10, 877- 882. (m) Song, Y.; Vittal, J. J.; Chan, S. H.; Leung, P. H. Organometallics 1999, 18, 650-655.
21. Many researchers including ourselves have used a conventional term "P-chiral" to express a chirality whose stereogenic center exists at the phosphorus atom. However, a referee of this paper recommended the use of "P-chirogenic" or "P-stereogenic" rather than "P-chiral", since chirality is a property of the molecule as a whole and not of a single atom. We agree with the referee's proposal and use the term "P-chirogenic" in this paper.
22. (a) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635-1636.
23. (b) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988-2989.
24. (c) Yamano, T.; Taya, N.; Kawada, M.; Huang, T.; Imamoto, T. Tetrahedron Lett. 1999, 40, 2577-2580.
25. Burk and co-workers have also demonstrated that bistrialkyl-phosphine ligands, 1,2-bis(trans-2,5-dialkylphospholano)ethanes (BPE), exhibit not only high enantioselectivity but also high catalytic efficiency in asymmetric hydrogenation. Burk, M. J. In Handbook of Chiral Chemicals; Ager, D. J., Ed.; Marcel Dekker: New York, 1999; Chapter 18 and references therein.
26. Electronic effects of trialkylphosphines in Rh-catalyzed hydrogenation were reported with some electronically modified ligands: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synthesis 1992, 169-178. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101-4102.
27. Electronic effects of trialkylphosphines in Rh-catalyzed hydrogenation were reported with some electronically modified ligands: (a) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synthesis 1992, 169-178. (b) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101-4102.
28. For new synthetic approaches of P-chirogenic phosphines bearing an aromatic substituent, see: (a) Juge, S.; Stephan, M.; Laffitte, J. A.; Genet, J. P. Tetrahedron Lett. 1990, 31, 6357-6360. (b) Corey, E. J.; Chen, Z.; Tanoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000-11001. (c) Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075-9076. (d) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293-9294. (e) Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116-5117.
29. For new synthetic approaches of P-chirogenic phosphines bearing an aromatic substituent, see: (a) Juge, S.; Stephan, M.; Laffitte, J. A.; Genet, J. P. Tetrahedron Lett. 1990, 31, 6357-6360. (b) Corey, E. J.; Chen, Z.; Tanoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000-11001. (c) Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075-9076. (d) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293-9294. (e) Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116-5117.
30. For new synthetic approaches of P-chirogenic phosphines bearing an aromatic substituent, see: (a) Juge, S.; Stephan, M.; Laffitte, J. A.; Genet, J. P. Tetrahedron Lett. 1990, 31, 6357-6360. (b) Corey, E. J.; Chen, Z.; Tanoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000-11001. (c) Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075-9076. (d) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293-9294. (e) Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116-5117.
31. For new synthetic approaches of P-chirogenic phosphines bearing an aromatic substituent, see: (a) Juge, S.; Stephan, M.; Laffitte, J. A.; Genet, J. P. Tetrahedron Lett. 1990, 31, 6357-6360. (b) Corey, E. J.; Chen, Z.; Tanoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000-11001. (c) Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075-9076. (d) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293-9294. (e) Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116-5117.
32. For new synthetic approaches of P-chirogenic phosphines bearing an aromatic substituent, see: (a) Juge, S.; Stephan, M.; Laffitte, J. A.; Genet, J. P. Tetrahedron Lett. 1990, 31, 6357-6360. (b) Corey, E. J.; Chen, Z.; Tanoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000-11001. (c) Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075-9076. (d) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293-9294. (e) Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116-5117.
33. Oshiki, T.; Hikosaka, T.; Imamoto, T. Tetrahedron Lett. 1991, 32, 3371-3374.
34. (1S)-exo-2-Bornanethiol was easily prepared from (-)-borneol in three steps and 60% overall yield: Blanco, J. M.; Caamaño, O.; Eirín, A.; Fernández, F.; Medina, L. Synthesis, 1990, 584-586.
35. (-)-Menthol, (+)-isomenthol, (+)-fenchyl alcohol, (-)-isopinocamphenol, (R)-1-phenylethylamine, and menthyltiol were also employed as chiral auxiliaries, but the obtained diastereomers were not separated completely.
36. The direct determination of ee values was not successful by chiral HPLC, and therefore their alkylated derivatives were used for the ee determinations.
37. (a) Bradley, D. C.; Hursthouse, M. B.; Motevalli, M.; Zheng, D. H. J. Chem. Soc., Chem. Commun. 1991, 7-8.
38. (b) Schmidbaur, H.; Wimmer, T.; Lachmann, J.; Müeller, G. Chem. Ber. 1991, 124, 275-278.
39. (c) Schmidbaur, H.; Stüetzer, A.; Bissinger, P.; Schier, A. Z. Anorg. Allg. Chem. 1993, 619, 1519-1525
40. (d) Gourdel, Y.; Pellon, P.; Toupet, L.; Le Corre, M. Tetrahedron Lett. 1994, 35, 1197-4294.
41. (e) Imamoto, T.; Hirakawa, E.; Yamanoi, Y.; Inoue, T.; Yamaguchi, K.; Seki, H. J. Org. Chem. 1995, 60, 7697-7700.
42. (f) Imamoto, T.; Yoshizawa, T.; Hirose, K.; Wada, Y.; Masuda, H.; Yamaguchi, K.; Seki, H. Heteroatom. Chem. 1995, 6, 99-104.
43. (g) Bader, A.; Pabel, M.; Willis, A. C.; Wild, S. B. Inorg. Chem. 1986, 35, 3874-3877.
44. (a) Valentine, D., Jr. In Asymmetric Synthesis; Morrison, J. D., Scott, J. W., Eds.; Academic Press: New York, 1984; Vol. 4, Chapter 3.
45. (b) Kagan, H. B.; Sasaki, M. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley & Sons: New York, 1990; Vol. 1, Chapter 3.
46. (c) Imamoto, T. In Handobook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992; Chapter 3.
47. The (S)-tert-butylmethylphosphine-borane possessing 89% ee was lithiated by butyllithium at 0°C, and the flask was immersed in a constant-temperature bath. After intervals ranging from 15 min to 2 h, a part of the solution was taken out and quenched with benzyl chloride. The enantiomeric excess of the derivative was determined by chiral HPLC (Daicel CHIRALCEL OD-H).
48. Baechler and Mislow reported that in tertiary phosphines the planar transition state of racemization was stabilized, relative to the ground state, by (p-p)π delocalization involving the lone pair of electrons on phosphorus: Baechler, R. D.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 3090-3093.
49. (a) Imamoto, T.; Kusumoto, T.; Suzuki, N.; Sato, K. J. Am. Chem. Soc. 1985, 107, 5301-5302.
50. (b) Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244-5252.
51. (c) Imamoto, T.; Oshiki, T.; Onozawa, T.; Matsuo, M.; Hikosaka, T.; Yanagawa, M. Heteroatom. Chem. 1992, 3, 563-575.
52. (d) Imamoto, T.; Matsuo, M.; Nonomura, T.; Kishikawa, K.; Yanagawa, M. Heteroatom. Chem. 1993, 4, 475-486.
53. (e) Soulier, E.; Clement, J. C.; Yaouanc, J. J.; des Abbayes, H. Tetrahedron Lett. 1998, 39, 4291-4294.
54. 8e However, this method was limited to the synthesis of one enantiomer.
55. 3 to afford the corresponding phosphines: (a) McKinstry, L.; Livinghouse, T. Tetrahedron Lett. 1994, 35, 9319-9322. (b) McKinstry, L.: Livinghouse, T. Tetrahedron 1995, 51, 7655-7666.
56. 3 to afford the corresponding phosphines: (a) McKinstry, L.; Livinghouse, T. Tetrahedron Lett. 1994, 35, 9319-9322. (b) McKinstry, L.: Livinghouse, T. Tetrahedron 1995, 51, 7655-7666.
57. 5a (21) Secondary phosphine-boranes used in these experiments were not enantiomerically pure, and hence small amounts of meso-isomers were produced.