Versatile chiral bidentate ligands derived from α-amino acids: Synthetic applications and mechanistic considerations in the palladium- mediated asymmetric allylic substitutions

Journal of Organic Chemistry

Volumn 65, Issue 14, 2000, Pages 4227-4240

  Saitoh, Akihito ^a   Achiwa, Kazuo ^a   Tanaka, Kiyoshi ^a   Morimoto, Toshiaki ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; AMIDE; N' [1 [(DIPHENYLPHOSPHINO)METHYL] 2 METHYL PROPYL] N,N' DIMETHYLMETHANIMIDAMIDE; PALLADIUM; UNCLASSIFIED DRUG; ALKALOID; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HALOGENATED HYDROCARBON;

AMINO ACID SUBSTITUTION; ARTICLE; CHIRALITY; COMPLEX FORMATION; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; LIGAND BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; CYCLOPROPANES; HYDROCARBONS, HALOGENATED; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0034647340     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991615l     Document Type: Article

References (113)

1. For pioneering studies, for example, see: (a) Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 4387. (b) Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 3821. (c) Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1977, 99, 1650.
2. For pioneering studies, for example, see: (a) Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 4387. (b) Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 3821. (c) Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1977, 99, 1650.
3. For pioneering studies, for example, see: (a) Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 4387. (b) Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 3821. (c) Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1977, 99, 1650.
4. Recent reviews including palladium-catalyzed allylic substitutions; see: (a) Wills, M.; Tye, H. J. Chem. Soc., Perkin Trans. 1 1999, 1109. (b) Wills, M. J. Chem. Soc., Perkin Trans. 1 1998, 3101. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705. (e) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic synthesis; John Wiley & Sons: New York, 1995; p 290. (f) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (g) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (h) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547. (i) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
5. Recent reviews including palladium-catalyzed allylic substitutions; see: (a) Wills, M.; Tye, H. J. Chem. Soc., Perkin Trans. 1 1999, 1109. (b) Wills, M. J. Chem. Soc., Perkin Trans. 1 1998, 3101. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705. (e) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic synthesis; John Wiley & Sons: New York, 1995; p 290. (f) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (g) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (h) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547. (i) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
6. Recent reviews including palladium-catalyzed allylic substitutions; see: (a) Wills, M.; Tye, H. J. Chem. Soc., Perkin Trans. 1 1999, 1109. (b) Wills, M. J. Chem. Soc., Perkin Trans. 1 1998, 3101. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705. (e) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic synthesis; John Wiley & Sons: New York, 1995; p 290. (f) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (g) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (h) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547. (i) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
7. Recent reviews including palladium-catalyzed allylic substitutions; see: (a) Wills, M.; Tye, H. J. Chem. Soc., Perkin Trans. 1 1999, 1109. (b) Wills, M. J. Chem. Soc., Perkin Trans. 1 1998, 3101. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705. (e) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic synthesis; John Wiley & Sons: New York, 1995; p 290. (f) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (g) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (h) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547. (i) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
8. Recent reviews including palladium-catalyzed allylic substitutions; see: (a) Wills, M.; Tye, H. J. Chem. Soc., Perkin Trans. 1 1999, 1109. (b) Wills, M. J. Chem. Soc., Perkin Trans. 1 1998, 3101. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705. (e) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic synthesis; John Wiley & Sons: New York, 1995; p 290. (f) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (g) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (h) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547. (i) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
9. Recent reviews including palladium-catalyzed allylic substitutions; see: (a) Wills, M.; Tye, H. J. Chem. Soc., Perkin Trans. 1 1999, 1109. (b) Wills, M. J. Chem. Soc., Perkin Trans. 1 1998, 3101. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705. (e) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic synthesis; John Wiley & Sons: New York, 1995; p 290. (f) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (g) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (h) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547. (i) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
10. Recent reviews including palladium-catalyzed allylic substitutions; see: (a) Wills, M.; Tye, H. J. Chem. Soc., Perkin Trans. 1 1999, 1109. (b) Wills, M. J. Chem. Soc., Perkin Trans. 1 1998, 3101. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705. (e) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic synthesis; John Wiley & Sons: New York, 1995; p 290. (f) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (g) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (h) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547. (i) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
11. Recent reviews including palladium-catalyzed allylic substitutions; see: (a) Wills, M.; Tye, H. J. Chem. Soc., Perkin Trans. 1 1999, 1109. (b) Wills, M. J. Chem. Soc., Perkin Trans. 1 1998, 3101. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705. (e) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic synthesis; John Wiley & Sons: New York, 1995; p 290. (f) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (g) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (h) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547. (i) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
12. Recent reviews including palladium-catalyzed allylic substitutions; see: (a) Wills, M.; Tye, H. J. Chem. Soc., Perkin Trans. 1 1999, 1109. (b) Wills, M. J. Chem. Soc., Perkin Trans. 1 1998, 3101. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (d) Williams, J. M. J. Synlett 1996, 705. (e) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic synthesis; John Wiley & Sons: New York, 1995; p 290. (f) Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (g) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. (h) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547. (i) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
13. Saitoh, A.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1997, 8, 3567. Recently, we abbreviated the amidine-phosphine hybrid ligand 7a derived from L-valine as "VALAP".
14. Achiwa, K. J. Am. Chem. Soc. 1976, 98, 8265.
15. A similar procedure to 10a was found in a previous publication byHiroi et al.; see: Hiroi, K.; Haraguchi, M.; Masuda, Y.; Abe, J. Chem. Lett. 1992, 2409.
16. Saitoh, A.; Misawa, M.; Morimoto, T. Synlett 1999, 483.
17. (a) Frost, C. G.; Williams, J. M. J. Tetrahedron Lett. 1993, 34, 2015.
18. (b) Frost, C. G.; Williams, J. M. J. Tetrahedron: Asymmetry 1993, 4, 1785.
19. (c) Dawson, G. J.; Frost, C. G.; Martin, C. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 7793.
20. (d) 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.
21. (e) Morimoto, T.; Tachibana, K.; Achiwa, K. Synlett 1997, 783.
22. (f) Chesney, A.; Bryce, M. R.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Tetrahedron: Asymmetry 1997, 8, 3185.
23. (g) Anderson, J. C.; James, D. S.; Mathias, J. P. Tetrahedron: Asymmetry 1998, 9, 753.
24. (h) Adams, H.; Anderson, J. C.; Cubbon, R; James, D. S.; Mathias, J. P. J. Org. Chem. 1999, 64, 8256.
25. (i) Boog-Wick, K.; Pregosin, P.; Trabesinger G. Organometallics 1998, 17, 3254.
26. Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
27. (a) Saitoh, A.; Misawa, M.; Morimoto, T. Tetrahedron: Asymmetry 1999, 10, 1025.
28. (b) Saitoh, A.; Uda, T.; Morimoto, T. Tetrahedron: Asymmetry 1999, 10, 4501.
29. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
30. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
31. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
32. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
33. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
34. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
35. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
36. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
37. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
38. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
39. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
40. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
41. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
42. For selected recent articles for P - N hybrid ligands, see: (a) Zhang W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343. (c) Cahill, J. P.; Gulry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301. (d) Widhalm, M.; Mereiter, K.; Bourghida, M. Tetrahedron: Asymmetry 1998, 9, 2983. (e) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465. (f) Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1779. (g) Bourghida, M.; Widhalm, M. Terahedron: Asymmetry 1998, 9, 1073. (h) Saitoh, A.; Achiwa, K.; Morimoto, T. Tetrahedron: Asymmetry 1998, 9, 741. (i) Kunz, H.; Glaser, B. Synlett 1998, 53. (j) Ahn, K. H.; Cho, C.-W.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179. (k) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Terahedron Lett. 1997, 38, 5971. (l) Sudo, A., Saigo, K. J. Org. Chem. 1997, 62, 5508. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583. (n) Gilbertson, S. R.; Chang, C.-W. T. Chem. Commun. 1997, 915.
43. (a) Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523.
44. (b) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry 1995, 6, 2535.
45. (a) von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566.
46. (b) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769.
47. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
48. (a) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200.
49. (b) Loiseleur, O.; Hayashi, M.; Schmees, N.; Pfaltz, A. Synthesis 1997, 1338.
50. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047.
51. (a) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493.
52. (b) Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron: Asymmetry 1991, 2, 663.
53. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143.
54. Commercially available dichloromethane with water content less than 30 ppm (WAKO Chemical) was employed for the present experiments.
55. For representative articles, see: (a) Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1986, 27, 4477. (b) Morimoto, T.; Takahashi, H.; Fujii, K.; Chiba, M.; Achiwa, K. Chem. Lett. 1986, 2061. (c) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1988, 29, 4755. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Takahashi, H.; Achiwa, K. Chem. Lett. 1989, 305. (f) Takahashi, H.; Morimoto, T.; Achiwa, K. J. Synth. Org. Chem., Jpn. 1990, 48, 29. (g) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169.
56. For representative articles, see: (a) Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1986, 27, 4477. (b) Morimoto, T.; Takahashi, H.; Fujii, K.; Chiba, M.; Achiwa, K. Chem. Lett. 1986, 2061. (c) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1988, 29, 4755. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Takahashi, H.; Achiwa, K. Chem. Lett. 1989, 305. (f) Takahashi, H.; Morimoto, T.; Achiwa, K. J. Synth. Org. Chem., Jpn. 1990, 48, 29. (g) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169.
57. For representative articles, see: (a) Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1986, 27, 4477. (b) Morimoto, T.; Takahashi, H.; Fujii, K.; Chiba, M.; Achiwa, K. Chem. Lett. 1986, 2061. (c) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1988, 29, 4755. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Takahashi, H.; Achiwa, K. Chem. Lett. 1989, 305. (f) Takahashi, H.; Morimoto, T.; Achiwa, K. J. Synth. Org. Chem., Jpn. 1990, 48, 29. (g) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169.
58. For representative articles, see: (a) Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1986, 27, 4477. (b) Morimoto, T.; Takahashi, H.; Fujii, K.; Chiba, M.; Achiwa, K. Chem. Lett. 1986, 2061. (c) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1988, 29, 4755. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Takahashi, H.; Achiwa, K. Chem. Lett. 1989, 305. (f) Takahashi, H.; Morimoto, T.; Achiwa, K. J. Synth. Org. Chem., Jpn. 1990, 48, 29. (g) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169.
59. For representative articles, see: (a) Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1986, 27, 4477. (b) Morimoto, T.; Takahashi, H.; Fujii, K.; Chiba, M.; Achiwa, K. Chem. Lett. 1986, 2061. (c) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1988, 29, 4755. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Takahashi, H.; Achiwa, K. Chem. Lett. 1989, 305. (f) Takahashi, H.; Morimoto, T.; Achiwa, K. J. Synth. Org. Chem., Jpn. 1990, 48, 29. (g) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169.
60. For representative articles, see: (a) Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1986, 27, 4477. (b) Morimoto, T.; Takahashi, H.; Fujii, K.; Chiba, M.; Achiwa, K. Chem. Lett. 1986, 2061. (c) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1988, 29, 4755. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Takahashi, H.; Achiwa, K. Chem. Lett. 1989, 305. (f) Takahashi, H.; Morimoto, T.; Achiwa, K. J. Synth. Org. Chem., Jpn. 1990, 48, 29. (g) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169.
61. For representative articles, see: (a) Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1986, 27, 4477. (b) Morimoto, T.; Takahashi, H.; Fujii, K.; Chiba, M.; Achiwa, K. Chem. Lett. 1986, 2061. (c) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1988, 29, 4755. (d) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9. (e) Takahashi, H.; Achiwa, K. Chem. Lett. 1989, 305. (f) Takahashi, H.; Morimoto, T.; Achiwa, K. J. Synth. Org. Chem., Jpn. 1990, 48, 29. (g) Inoguchi, K.; Sakuraba, S.; Achiwa, K. Synlett 1992, 169.
62. For instance, for asymmetric hydrogenations, see: (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. (b) RajanBabu, T. V.; Radetich, B.; You K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. Asymmetric epoxidations, see: (c) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (d) Sasaki, H.; Irie, R.; Katsuki, T. Synlett 1994, 356. Asymmetric hydrosilylations, see: (e) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. Asymmetric hydrocyanations, see: (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (g) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1996, 118, 6325.
63. For instance, for asymmetric hydrogenations, see: (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. (b) RajanBabu, T. V.; Radetich, B.; You K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. Asymmetric epoxidations, see: (c) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (d) Sasaki, H.; Irie, R.; Katsuki, T. Synlett 1994, 356. Asymmetric hydrosilylations, see: (e) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. Asymmetric hydrocyanations, see: (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (g) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1996, 118, 6325.
64. For instance, for asymmetric hydrogenations, see: (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. (b) RajanBabu, T. V.; Radetich, B.; You K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. Asymmetric epoxidations, see: (c) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (d) Sasaki, H.; Irie, R.; Katsuki, T. Synlett 1994, 356. Asymmetric hydrosilylations, see: (e) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. Asymmetric hydrocyanations, see: (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (g) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1996, 118, 6325.
65. For instance, for asymmetric hydrogenations, see: (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. (b) RajanBabu, T. V.; Radetich, B.; You K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. Asymmetric epoxidations, see: (c) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (d) Sasaki, H.; Irie, R.; Katsuki, T. Synlett 1994, 356. Asymmetric hydrosilylations, see: (e) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. Asymmetric hydrocyanations, see: (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (g) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1996, 118, 6325.
66. For instance, for asymmetric hydrogenations, see: (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. (b) RajanBabu, T. V.; Radetich, B.; You K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. Asymmetric epoxidations, see: (c) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (d) Sasaki, H.; Irie, R.; Katsuki, T. Synlett 1994, 356. Asymmetric hydrosilylations, see: (e) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. Asymmetric hydrocyanations, see: (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (g) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1996, 118, 6325.
67. For instance, for asymmetric hydrogenations, see: (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. (b) RajanBabu, T. V.; Radetich, B.; You K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. Asymmetric epoxidations, see: (c) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (d) Sasaki, H.; Irie, R.; Katsuki, T. Synlett 1994, 356. Asymmetric hydrosilylations, see: (e) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. Asymmetric hydrocyanations, see: (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (g) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1996, 118, 6325.
68. For instance, for asymmetric hydrogenations, see: (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101. (b) RajanBabu, T. V.; Radetich, B.; You K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429. Asymmetric epoxidations, see: (c) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (d) Sasaki, H.; Irie, R.; Katsuki, T. Synlett 1994, 356. Asymmetric hydrosilylations, see: (e) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306. Asymmetric hydrocyanations, see: (f) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1992, 114, 6265. (g) RajanBabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1996, 118, 6325.
69. (a) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895.
70. (b) Nomura, N.; Mermet-Bouvier, Y. C.; RajanBabu, T. V. Synlett 1996, 745.
71. (c) Porte, A. M.; Reibenspies, J.; Burgess, K. J. Am. Chem. Soc. 1998, 120, 9180.
72. Kurosawa, H.; Majima, T.; Asada, N. J. Am. Chem. Soc. 1980, 102, 6996.
73. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089.
74. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem Commun. 1995, 1845.
75. (c) Dierkes, P.; Ramdeehul, S.; Barloy, L.; Cian, A. D.; Fischer, J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 3116.
76. For asymmetric allylations of cycloalkenyl substrates by phosphanyldihydrooxazoles, see: (a) Sennhenn, P.; Gabler, B.; Helmchen, G. Tetrahedron Lett. 1994, 35, 8595. (b) Gilbertson, S. R.; Chang, C.- W. T. J. Org. Chem. 1998, 63, 8424. By other P - N hybrid ligands, see refs 10g and 15a.
77. For asymmetric allylations of cycloalkenyl substrates by phosphanyldihydrooxazoles, see: (a) Sennhenn, P.; Gabler, B.; Helmchen, G. Tetrahedron Lett. 1994, 35, 8595. (b) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424. By other P - N hybrid ligands, see refs 10g and 15a.
78. (a) Fiaud, J.-C.; Aribi-Zouioueche, L. J. Organomet. Chem. 1985, 295, 383.
79. (b) Fiaud, J.-C.; Legros, J.-Y. Tetrahedron Lett. 1991, 32, 5089.
80. (c) Fotiadu, F.; Cros, P.; Faure, B.; Buono, G. Tetrahedron Lett. 1990, 31, 77.
81. Palladium-catalyzed allylic substitutions using KSA and achiral ligands, see: (a) Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1983, 1325. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793. (c) Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797. (d) Tsuji, J.; Takahashi, K.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 4783. (e) Carfagna, C.; Mariani, L.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 3924. (c) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. J. Mol. Catal. 1992, 72, 19. For iron complexes for the reaction of allyl acetate with KSA, see: (g) Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B. B. J. Org. Chem. 1996, 61, 147. Molybdenum- and tungsten-catalyzed allylic substitutions, see: Malkov, A. V.; Baxendale, I. R.; Dvorák, D.; Mansfield, D. J.; Kocovsky, P. J. Org. Chem. 1999, 64, 2737.
82. Palladium-catalyzed allylic substitutions using KSA and achiral ligands, see: (a) Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1983, 1325. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793. (c) Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797. (d) Tsuji, J.; Takahashi, K.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 4783. (e) Carfagna, C.; Mariani, L.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 3924. (c) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. J. Mol. Catal. 1992, 72, 19. For iron complexes for the reaction of allyl acetate with KSA, see: (g) Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B. B. J. Org. Chem. 1996, 61, 147. Molybdenum- and tungsten-catalyzed allylic substitutions, see: Malkov, A. V.; Baxendale, I. R.; Dvorák, D.; Mansfield, D. J.; Kocovsky, P. J. Org. Chem. 1999, 64, 2737.
83. Palladium-catalyzed allylic substitutions using KSA and achiral ligands, see: (a) Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1983, 1325. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793. (c) Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797. (d) Tsuji, J.; Takahashi, K.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 4783. (e) Carfagna, C.; Mariani, L.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 3924. (c) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. J. Mol. Catal. 1992, 72, 19. For iron complexes for the reaction of allyl acetate with KSA, see: (g) Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B. B. J. Org. Chem. 1996, 61, 147. Molybdenum- and tungsten-catalyzed allylic substitutions, see: Malkov, A. V.; Baxendale, I. R.; Dvorák, D.; Mansfield, D. J.; Kocovsky, P. J. Org. Chem. 1999, 64, 2737.
84. Palladium-catalyzed allylic substitutions using KSA and achiral ligands, see: (a) Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1983, 1325. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793. (c) Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797. (d) Tsuji, J.; Takahashi, K.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 4783. (e) Carfagna, C.; Mariani, L.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 3924. (c) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. J. Mol. Catal. 1992, 72, 19. For iron complexes for the reaction of allyl acetate with KSA, see: (g) Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B. B. J. Org. Chem. 1996, 61, 147. Molybdenum- and tungsten-catalyzed allylic substitutions, see: Malkov, A. V.; Baxendale, I. R.; Dvorák, D.; Mansfield, D. J.; Kocovsky, P. J. Org. Chem. 1999, 64, 2737.
85. Palladium-catalyzed allylic substitutions using KSA and achiral ligands, see: (a) Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1983, 1325. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793. (c) Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797. (d) Tsuji, J.; Takahashi, K.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 4783. (e) Carfagna, C.; Mariani, L.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 3924. (c) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. J. Mol. Catal. 1992, 72, 19. For iron complexes for the reaction of allyl acetate with KSA, see: (g) Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B. B. J. Org. Chem. 1996, 61, 147. Molybdenum- and tungsten-catalyzed allylic substitutions, see: Malkov, A. V.; Baxendale, I. R.; Dvorák, D.; Mansfield, D. J.; Kocovsky, P. J. Org. Chem. 1999, 64, 2737.
86. Palladium-catalyzed allylic substitutions using KSA and achiral ligands, see: (a) Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1983, 1325. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793. (c) Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797. (d) Tsuji, J.; Takahashi, K.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 4783. (e) Carfagna, C.; Mariani, L.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 3924. (c) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. J. Mol. Catal. 1992, 72, 19. For iron complexes for the reaction of allyl acetate with KSA, see: (g) Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B. B. J. Org. Chem. 1996, 61, 147. Molybdenum- and tungsten-catalyzed allylic substitutions, see: Malkov, A. V.; Baxendale, I. R.; Dvorák, D.; Mansfield, D. J.; Kocovsky, P. J. Org. Chem. 1999, 64, 2737.
87. Palladium-catalyzed allylic substitutions using KSA and achiral ligands, see: (a) Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1983, 1325. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793. (c) Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797. (d) Tsuji, J.; Takahashi, K.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 4783. (e) Carfagna, C.; Mariani, L.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 3924. (c) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. J. Mol. Catal. 1992, 72, 19. For iron complexes for the reaction of allyl acetate with KSA, see: (g) Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B. B. J. Org. Chem. 1996, 61, 147. Molybdenum- and tungsten-catalyzed allylic substitutions, see: Malkov, A. V.; Baxendale, I. R.; Dvorák, D.; Mansfield, D. J.; Kocovsky, P. J. Org. Chem. 1999, 64, 2737.
88. Palladium-catalyzed allylic substitutions using KSA and achiral ligands, see: (a) Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1983, 1325. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793. (c) Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797. (d) Tsuji, J.; Takahashi, K.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 4783. (e) Carfagna, C.; Mariani, L.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 3924. (c) Carfagna, C.; Galarini, R.; Musco, A.; Santi, R. J. Mol. Catal. 1992, 72, 19. For iron complexes for the reaction of allyl acetate with KSA, see: (g) Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B. B. J. Org. Chem. 1996, 61, 147. Molybdenum- and tungsten-catalyzed allylic substitutions, see: Malkov, A. V.; Baxendale, I. R.; Dvorák, D.; Mansfield, D. J.; Kocovsky, P. J. Org. Chem. 1999, 64, 2737.
89. Ketene methyltrimethylsilyl acetal 19c was prepared as a 7:3 mixture with a C-silylated compound, methyltrimethylsilyl acetate. Carbomethoxy ketene methyltrimethylsilyl acetal 19d tends to be hydrolyzed easily. Therefore, the hydrolyzed product dimethyl malonate was removed by distillation just before conducting the asymmetric reaction. For articles referring to the preparation of ketene silyl acetals, see: (a) Ainsworth, C.; Chen, F.; Kuo, Y.-N. J. Organomet. Chem. 1972, 46, 59. (b) Rathke, M. W.; Sullivan, D. F. Synth. Commun. 1973, 3, 67. (c) Kita, Y.; Haruta, J.; Segawa, J.; Tamura, Y. Tetrahedron Lett. 1979, 4311.
90. Ketene methyltrimethylsilyl acetal 19c was prepared as a 7:3 mixture with a C-silylated compound, methyltrimethylsilyl acetate. Carbomethoxy ketene methyltrimethylsilyl acetal 19d tends to be hydrolyzed easily. Therefore, the hydrolyzed product dimethyl malonate was removed by distillation just before conducting the asymmetric reaction. For articles referring to the preparation of ketene silyl acetals, see: (a) Ainsworth, C.; Chen, F.; Kuo, Y.-N. J. Organomet. Chem. 1972, 46, 59. (b) Rathke, M. W.; Sullivan, D. F. Synth. Commun. 1973, 3, 67. (c) Kita, Y.; Haruta, J.; Segawa, J.; Tamura, Y. Tetrahedron Lett. 1979, 4311.
91. Ketene methyltrimethylsilyl acetal 19c was prepared as a 7:3 mixture with a C-silylated compound, methyltrimethylsilyl acetate. Carbomethoxy ketene methyltrimethylsilyl acetal 19d tends to be hydrolyzed easily. Therefore, the hydrolyzed product dimethyl malonate was removed by distillation just before conducting the asymmetric reaction. For articles referring to the preparation of ketene silyl acetals, see: (a) Ainsworth, C.; Chen, F.; Kuo, Y.-N. J. Organomet. Chem. 1972, 46, 59. (b) Rathke, M. W.; Sullivan, D. F. Synth. Commun. 1973, 3, 67. (c) Kita, Y.; Haruta, J.; Segawa, J.; Tamura, Y. Tetrahedron Lett. 1979, 4311.
92. Kühn, O.; Mayr, H. Angew. Chem., Int. Ed. Engl. 1999, 38, 343.
93. It has been demonstrated in the study for X-ray crystal structures of tetraalkylammonium enolates derived from malonates that the enolates present as dimeric structure even if the crystal was formed in DMSO; see: Reetz, M. T.; Hütte, S.; Goddard, R. J. Am. Chem. Soc. 1993, 115, 9339.
94. (a) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. Am. Chem. Soc. 1978, 100, 3435.
95. (b) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1978, 100, 3416.
96. (c) Trost, B. M.; Verhoeven, T. R. J. Am. Chem Soc. 1980, 102, 4730.
97. (d) Hayashi, T.; Hagihara, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1983, 105, 7767.
98. (e) Åkermark, B.; Bäckvall, J. E.; Lowenborg, A.; Zetterberg, K. J. Organomet. Chem. 1979, 766, C33.
99. (f) Åkermark, B.; Jutand, A. J. Organomet. Chem. 1981, 217, C41.
100. (a) von Matt, P.; Lloyd-Jones, G.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Regger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265.
101. (b) Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2108.
102. (a) Sakuraba, S.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1991, 2, 597. The P/M chirality concept was further generalized by Pz(plus zone)/Mz(minus zone) chirality concept in which the course of reaction in asymmetric hydrogenations using chiral bisphospholane ligands could be well explained.
103. (b) Achiwa, K. Principles and Applications of Chiral Technology; Industrial Publishing & Consulting: Japan, 1999.
104. (c) Fujie, N.; Matsui, M.; Achiwa, K. Chem. Pharm. Bull. 1999, 47, 436.
105. Crystal structures of palladium - BINAP complexes have been elucidated by several groups, in which equatorial phenyl substituents on each phosphorus atom of (S)-BINAP are found to occupy the positions assignable to Mr chirality; see: (a) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. (b) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83. (c) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 5040. (d) Yamaguchi, M.; Yabuki, M.; Yamagishi, T.; Sakai, K.; Tsubomura, T. Chem. Lett. 1996, 241. (e) Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 3236. In ref 32b,c, structural studies for palladium - (S,S)- Chiraphos complexes were presented using multidimensional NMR spectroscopy and MM2 calculations. On the basis of these data, Mr chirality of (S,S)-Chiraphos was pointed out although less equatorial and axial character was demonstrated compared with the palladium - BINAP complex. Moreover, the X-ray crystal structure of rhodium complex with (R,R)-Chiraphos suggests that the ligand has two equatrial phenyl groups at the Pr position; see. Halpern, J. In Asymmetric Synthesis Vol. 5; Morruson, J. D., Ed.; Academic Press: New York, 1985. It is reasonable that (S,S)-Norphos is assigned to have Mr chirality from a similarity of molecular structure to (S,S)-Chiraphos. The results in rhodium-catalyzed asymmetric hydrogenation of N-benzoylhydrazone using (R,R)-Norphos also supported the assignment; see: Yamazaki, A.; Achiwa, I.; Horikawa, K.; Tsurubo, M.; Achiwa, K. Synlett 1997, 455.
106. Crystal structures of palladium - BINAP complexes have been elucidated by several groups, in which equatorial phenyl substituents on each phosphorus atom of (S)-BINAP are found to occupy the positions assignable to Mr chirality; see: (a) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. (b) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83. (c) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 5040. (d) Yamaguchi, M.; Yabuki, M.; Yamagishi, T.; Sakai, K.; Tsubomura, T. Chem. Lett. 1996, 241. (e) Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 3236. In ref 32b,c, structural studies for palladium - (S,S)- Chiraphos complexes were presented using multidimensional NMR spectroscopy and MM2 calculations. On the basis of these data, Mr chirality of (S,S)-Chiraphos was pointed out although less equatorial and axial character was demonstrated compared with the palladium - BINAP complex. Moreover, the X-ray crystal structure of rhodium complex with (R,R)-Chiraphos suggests that the ligand has two equatrial phenyl groups at the Pr position; see. Halpern, J. In Asymmetric Synthesis Vol. 5; Morruson, J. D., Ed.; Academic Press: New York, 1985. It is reasonable that (S,S)-Norphos is assigned to have Mr chirality from a similarity of molecular structure to (S,S)-Chiraphos. The results in rhodium-catalyzed asymmetric hydrogenation of N-benzoylhydrazone using (R,R)-Norphos also supported the assignment; see: Yamazaki, A.; Achiwa, I.; Horikawa, K.; Tsurubo, M.; Achiwa, K. Synlett 1997, 455.
107. Crystal structures of palladium - BINAP complexes have been elucidated by several groups, in which equatorial phenyl substituents on each phosphorus atom of (S)-BINAP are found to occupy the positions assignable to Mr chirality; see: (a) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. (b) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83. (c) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 5040. (d) Yamaguchi, M.; Yabuki, M.; Yamagishi, T.; Sakai, K.; Tsubomura, T. Chem. Lett. 1996, 241. (e) Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 3236. In ref 32b,c, structural studies for palladium - (S,S)- Chiraphos complexes were presented using multidimensional NMR spectroscopy and MM2 calculations. On the basis of these data, Mr chirality of (S,S)-Chiraphos was pointed out although less equatorial and axial character was demonstrated compared with the palladium - BINAP complex. Moreover, the X-ray crystal structure of rhodium complex with (R,R)-Chiraphos suggests that the ligand has two equatrial phenyl groups at the Pr position; see. Halpern, J. In Asymmetric Synthesis Vol. 5; Morruson, J. D., Ed.; Academic Press: New York, 1985. It is reasonable that (S,S)-Norphos is assigned to have Mr chirality from a similarity of molecular structure to (S,S)-Chiraphos. The results in rhodium-catalyzed asymmetric hydrogenation of N-benzoylhydrazone using (R,R)-Norphos also supported the assignment; see: Yamazaki, A.; Achiwa, I.; Horikawa, K.; Tsurubo, M.; Achiwa, K. Synlett 1997, 455.
108. Crystal structures of palladium - BINAP complexes have been elucidated by several groups, in which equatorial phenyl substituents on each phosphorus atom of (S)-BINAP are found to occupy the positions assignable to Mr chirality; see: (a) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. (b) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83. (c) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 5040. (d) Yamaguchi, M.; Yabuki, M.; Yamagishi, T.; Sakai, K.; Tsubomura, T. Chem. Lett. 1996, 241. (e) Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 3236. In ref 32b,c, structural studies for palladium - (S,S)- Chiraphos complexes were presented using multidimensional NMR spectroscopy and MM2 calculations. On the basis of these data, Mr chirality of (S,S)-Chiraphos was pointed out although less equatorial and axial character was demonstrated compared with the palladium - BINAP complex. Moreover, the X-ray crystal structure of rhodium complex with (R,R)-Chiraphos suggests that the ligand has two equatrial phenyl groups at the Pr position; see. Halpern, J. In Asymmetric Synthesis Vol. 5; Morruson, J. D., Ed.; Academic Press: New York, 1985. It is reasonable that (S,S)-Norphos is assigned to have Mr chirality from a similarity of molecular structure to (S,S)-Chiraphos. The results in rhodium-catalyzed asymmetric hydrogenation of N-benzoylhydrazone using (R,R)-Norphos also supported the assignment; see: Yamazaki, A.; Achiwa, I.; Horikawa, K.; Tsurubo, M.; Achiwa, K. Synlett 1997, 455.
109. Crystal structures of palladium - BINAP complexes have been elucidated by several groups, in which equatorial phenyl substituents on each phosphorus atom of (S)-BINAP are found to occupy the positions assignable to Mr chirality; see: (a) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. (b) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83. (c) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 5040. (d) Yamaguchi, M.; Yabuki, M.; Yamagishi, T.; Sakai, K.; Tsubomura, T. Chem. Lett. 1996, 241. (e) Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 3236. In ref 32b,c, structural studies for palladium - (S,S)-Chiraphos complexes were presented using multidimensional NMR spectroscopy and MM2 calculations. On the basis of these data, Mr chirality of (S,S)-Chiraphos was pointed out although less equatorial and axial character was demonstrated compared with the palladium -BINAP complex. Moreover, the X-ray crystal structure of rhodium complex with (R,R)-Chiraphos suggests that the ligand has two equatrial phenyl groups at the Pr position; see. Halpern, J. In Asymmetric Synthesis Vol. 5; Morruson, J. D., Ed.; Academic Press: New York, 1985. It is reasonable that (S,S)-Norphos is assigned to have Mr chirality from a similarity of molecular structure to (S,S)-Chiraphos. The results in rhodium-catalyzed asymmetric hydrogenation of N-benzoylhydrazone using (R,R)-Norphos also supported the assignment; see: Yamazaki, A.; Achiwa, I.; Horikawa, K.; Tsurubo, M.; Achiwa, K. Synlett 1997, 455.
110. Crystal structures of palladium - BINAP complexes have been elucidated by several groups, in which equatorial phenyl substituents on each phosphorus atom of (S)-BINAP are found to occupy the positions assignable to Mr chirality; see: (a) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. (b) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83. (c) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 5040. (d) Yamaguchi, M.; Yabuki, M.; Yamagishi, T.; Sakai, K.; Tsubomura, T. Chem. Lett. 1996, 241. (e) Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 3236. In ref 32b,c, structural studies for palladium - (S,S)- Chiraphos complexes were presented using multidimensional NMR spectroscopy and MM2 calculations. On the basis of these data, Mr chirality of (S,S)-Chiraphos was pointed out although less equatorial and axial character was demonstrated compared with the palladium - BINAP complex. Moreover, the X-ray crystal structure of rhodium complex with (R,R)-Chiraphos suggests that the ligand has two equatrial phenyl groups at the Pr position; see. Halpern, J. In Asymmetric Synthesis Vol. 5; Morruson, J. D., Ed.; Academic Press: New York, 1985. It is reasonable that (S,S)-Norphos is assigned to have Mr chirality from a similarity of molecular structure to (S,S)-Chiraphos. The results in rhodium-catalyzed asymmetric hydrogenation of N-benzoylhydrazone using (R,R)-Norphos also supported the assignment; see: Yamazaki, A.; Achiwa, I.; Horikawa, K.; Tsurubo, M.; Achiwa, K. Synlett 1997, 455.
111. Crystal structures of palladium - BINAP complexes have been elucidated by several groups, in which equatorial phenyl substituents on each phosphorus atom of (S)-BINAP are found to occupy the positions assignable to Mr chirality; see:
112. Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347.
113. The X-ray crystal structure of a rhodium complex with a P - N hybrid ligand based on L-valine consisting of bis (4-methylphenyl)-phosphino and 4-methoxybenzylamino groups indicates that the ligand has Mr chirality; see: Berger, H.; Nesper, R.; Pregosin, P. S.; Rüegger, H.; Wörle, M. Helv. Chim. Acta 1993, 76, 1520.