Optically pure 1,2-bis[(o-alkylphenyl)phenylphosphino]ethanes and their use in rhodium-catalyzed asymmetric hydrogenations of α-(acylamino)acrylic derivatives

Advanced Synthesis and Catalysis

Volumn 346, Issue 7, 2004, Pages 777-788

  Wada, Yoshiyuki ^a,b   Imamoto, Tsuneo ^a   Tsuruta, Hideyuki ^a   Yamaguchi, Kentaro ^a   Gridnev, Ilya D ^c  

^a CHIBA UNIVERSITY   (Japan)

^b Flavor System and Technology Laboratory   (Japan)

^c TOHOKU UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Asymmetric hydrogenation; Enantioselectivity; P stereogenic ligands; Rhodium catalysts

Indexed keywords

1,2 BIS[(2 METHOXYPHENYL)PHENYLPHOSPHINO]ETHANE; 1,2 BIS[PHENYL (5',6',7',8' TETRAHYDRONAPHTHYL)PHOSPHINO]ETHANE; ACRYLIC ACID DERIVATIVE; ALKYLBENZENE; BENZENE DERIVATIVE; BORANE DERIVATIVE; ETHANE; N ACYLAMINO ACID; NAPHTHYL GROUP; PHENYL GROUP; PHOSPHINE DERIVATIVE; PHOSPHORUS; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; ENANTIOSELECTIVITY; HYDROGENATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 4143124245     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404043     Document Type: Article

References (61)

1. nd edn., (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 1; e) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, Vols. 1-3; f) R. Noyori, Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, New York, 1994; g) H. B. Kagan, in: Asymmetric Synthesis, Vol. 5, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chap. 1.
2. nd edn., (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 1; e) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, Vols. 1-3; f) R. Noyori, Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, New York, 1994; g) H. B. Kagan, in: Asymmetric Synthesis, Vol. 5, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chap. 1.
3. nd edn., (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 1; e) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, Vols. 1-3; f) R. Noyori, Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, New York, 1994; g) H. B. Kagan, in: Asymmetric Synthesis, Vol. 5, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chap. 1.
4. nd edn., (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 1; e) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, Vols. 1-3; f) R. Noyori, Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, New York, 1994; g) H. B. Kagan, in: Asymmetric Synthesis, Vol. 5, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chap. 1.
5. nd edn., (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 1; e) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, Vols. 1-3; f) R. Noyori, Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, New York, 1994; g) H. B. Kagan, in: Asymmetric Synthesis, Vol. 5, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chap. 1.
6. nd edn., (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 1; e) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, Vols. 1-3; f) R. Noyori, Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, New York, 1994; g) H. B. Kagan, in: Asymmetric Synthesis, Vol. 5, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chap. 1.
7. nd edn., (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 1; e) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, Vols. 1-3; f) R. Noyori, Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, New York, 1994; g) H. B. Kagan, in: Asymmetric Synthesis, Vol. 5, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chap. 1.
8. nd edn., (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 1; e) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, Vols. 1-3; f) R. Noyori, Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, New York, 1994; g) H. B. Kagan, in: Asymmetric Synthesis, Vol. 5, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chap. 1.
9. For representative reviews dealing with optically active phosphine ligands as the main subject, see: a) G. Chelucci, G. Orrù, G. A. Pinna, Tetrahedron 2003, 59, 9471; b) K. V. L. Crépy, T. Imamoto, Top. Curr. Chem. 2003, 229, 1; c) M. Ohff, J. Holz, M. Quirmbach, A. Börner, Synthesis 1998, 1391; d) D. Laurenti, M. Santelli, Org. Prep. Proc. Int. 1999, 31, 245; e) A. Marinetti, D. Carmichael, Chem. Rev. 2002, #102#92, 201; f) J. Holz, M. Quirmbach, A. Börner, Synthesis 1997, 981; g) J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995; h) K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375; i) H. B. Kagan, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Vol. 5, Chap. 1; j) D. J. Valentine, in: Asymmetric Synthesis, (Eds.: J. D. Morrison, J. W. Scott), Academic Press, New York, 1984, Vol. 4, Chap. 3.
10. For representative reviews dealing with optically active phosphine ligands as the main subject, see: a) G. Chelucci, G. Orrù, G. A. Pinna, Tetrahedron 2003, 59, 9471; b) K. V. L. Crépy, T. Imamoto, Top. Curr. Chem. 2003, 229, 1; c) M. Ohff, J. Holz, M. Quirmbach, A. Börner, Synthesis 1998, 1391; d) D. Laurenti, M. Santelli, Org. Prep. Proc. Int. 1999, 31, 245; e) A. Marinetti, D. Carmichael, Chem. Rev. 2002, #102#92, 201; f) J. Holz, M. Quirmbach, A. Börner, Synthesis 1997, 981; g) J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995; h) K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375; i) H. B. Kagan, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Vol. 5, Chap. 1; j) D. J. Valentine, in: Asymmetric Synthesis, (Eds.: J. D. Morrison, J. W. Scott), Academic Press, New York, 1984, Vol. 4, Chap. 3.
11. For representative reviews dealing with optically active phosphine ligands as the main subject, see: a) G. Chelucci, G. Orrù, G. A. Pinna, Tetrahedron 2003, 59, 9471; b) K. V. L. Crépy, T. Imamoto, Top. Curr. Chem. 2003, 229, 1; c) M. Ohff, J. Holz, M. Quirmbach, A. Börner, Synthesis 1998, 1391; d) D. Laurenti, M. Santelli, Org. Prep. Proc. Int. 1999, 31, 245; e) A. Marinetti, D. Carmichael, Chem. Rev. 2002, #102#92, 201; f) J. Holz, M. Quirmbach, A. Börner, Synthesis 1997, 981; g) J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995; h) K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375; i) H. B. Kagan, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Vol. 5, Chap. 1; j) D. J. Valentine, in: Asymmetric Synthesis, (Eds.: J. D. Morrison, J. W. Scott), Academic Press, New York, 1984, Vol. 4, Chap. 3.
12. For representative reviews dealing with optically active phosphine ligands as the main subject, see: a) G. Chelucci, G. Orrù, G. A. Pinna, Tetrahedron 2003, 59, 9471; b) K. V. L. Crépy, T. Imamoto, Top. Curr. Chem. 2003, 229, 1; c) M. Ohff, J. Holz, M. Quirmbach, A. Börner, Synthesis 1998, 1391; d) D. Laurenti, M. Santelli, Org. Prep. Proc. Int. 1999, 31, 245; e) A. Marinetti, D. Carmichael, Chem. Rev. 2002, #102#92, 201; f) J. Holz, M. Quirmbach, A. Börner, Synthesis 1997, 981; g) J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995; h) K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375; i) H. B. Kagan, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Vol. 5, Chap. 1; j) D. J. Valentine, in: Asymmetric Synthesis, (Eds.: J. D. Morrison, J. W. Scott), Academic Press, New York, 1984, Vol. 4, Chap. 3.
13. For representative reviews dealing with optically active phosphine ligands as the main subject, see: a) G. Chelucci, G. Orrù, G. A. Pinna, Tetrahedron 2003, 59, 9471; b) K. V. L. Crépy, T. Imamoto, Top. Curr. Chem. 2003, 229, 1; c) M. Ohff, J. Holz, M. Quirmbach, A. Börner, Synthesis 1998, 1391; d) D. Laurenti, M. Santelli, Org. Prep. Proc. Int. 1999, 31, 245; e) A. Marinetti, D. Carmichael, Chem. Rev. 2002, #102#92, 201; f) J. Holz, M. Quirmbach, A. Börner, Synthesis 1997, 981; g) J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995; h) K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375; i) H. B. Kagan, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Vol. 5, Chap. 1; j) D. J. Valentine, in: Asymmetric Synthesis, (Eds.: J. D. Morrison, J. W. Scott), Academic Press, New York, 1984, Vol. 4, Chap. 3.
14. For representative reviews dealing with optically active phosphine ligands as the main subject, see: a) G. Chelucci, G. Orrù, G. A. Pinna, Tetrahedron 2003, 59, 9471; b) K. V. L. Crépy, T. Imamoto, Top. Curr. Chem. 2003, 229, 1; c) M. Ohff, J. Holz, M. Quirmbach, A. Börner, Synthesis 1998, 1391; d) D. Laurenti, M. Santelli, Org. Prep. Proc. Int. 1999, 31, 245; e) A. Marinetti, D. Carmichael, Chem. Rev. 2002, #102#92, 201; f) J. Holz, M. Quirmbach, A. Börner, Synthesis 1997, 981; g) J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995; h) K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375; i) H. B. Kagan, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Vol. 5, Chap. 1; j) D. J. Valentine, in: Asymmetric Synthesis, (Eds.: J. D. Morrison, J. W. Scott), Academic Press, New York, 1984, Vol. 4, Chap. 3.
15. For representative reviews dealing with optically active phosphine ligands as the main subject, see: a) G. Chelucci, G. Orrù, G. A. Pinna, Tetrahedron 2003, 59, 9471; b) K. V. L. Crépy, T. Imamoto, Top. Curr. Chem. 2003, 229, 1; c) M. Ohff, J. Holz, M. Quirmbach, A. Börner, Synthesis 1998, 1391; d) D. Laurenti, M. Santelli, Org. Prep. Proc. Int. 1999, 31, 245; e) A. Marinetti, D. Carmichael, Chem. Rev. 2002, #102#92, 201; f) J. Holz, M. Quirmbach, A. Börner, Synthesis 1997, 981; g) J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995; h) K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375; i) H. B. Kagan, in: Asymmetric Synthesis, (Ed.: J. D. Morrison), Academic Press, New York, 1985, Vol. 5, Chap. 1; j) D. J. Valentine, in: Asymmetric Synthesis, (Eds.: J. D. Morrison, J. W. Scott), Academic Press, New York, 1984, Vol. 4, Chap. 3.
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33. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
34. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
35. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
36. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
37. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
38. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
39. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
40. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
41. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
42. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
43. For other representative P-stereogenic phosphine ligands used for asymmetric catalysis, see: a) L. Horner, B. Schlotthauer, Phosphorus Sulfur 1978, 4, 155; b) J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Townsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086; c) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; d) T. Imamoto, J. Watanabe, Y. Wada, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635; e) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1999, 64, 2988; f) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833; g) I. D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, T. Imamoto, Adv. Synth. Catal. 2001, 343, 118; h) A. Ohashi, T. Imamoto, Org. Lett. 2001, 3, 373; i) T. Imamoto, Pure Appl. Chem. 2001, 73, 373; j) W. Tang, X. Zhang, Angew. Chem. Int. Ed. 2002, 41, 1612; k) T. Hamada; S. L. Buchwald, Org. Lett. 2002, 4, 999; l) W. Tang, W. Wang, X. Zhang, Angew. Chem. Int. Ed. 2003, 42, 943.
44. [7] and B. McCulloch, J. Halpern, M. R. Thompson, C. R. Landis, Organometallics 1990, 9, 1392.
45. A preliminary account of a portion of this work has been described: T. Imamoto, H. Tsuruta, Y. Wada, H. Masuda, K. Yamaguchi, Tetrahedron Lett. 1995, 36, 8271.
46. T. Imamoto, T. Kusumoto, N. Suzuki, K. Sato, J. Am. Chem. Soc. 1985, 107, 5301; T. Imamoto, T. Oshiki, T. Onozawa, T. Kusumoto, K. Sato, J. Am. Chem. Soc. 1990, 112, 5244.
47. T. Imamoto, T. Kusumoto, N. Suzuki, K. Sato, J. Am. Chem. Soc. 1985, 107, 5301; T. Imamoto, T. Oshiki, T. Onozawa, T. Kusumoto, K. Sato, J. Am. Chem. Soc. 1990, 112, 5244.
48. The removal of the boranato group from phosphine-boranes by the use of amines is limited to the compounds bearing aryl groups. Deboranation of trialkylphosphine-boranes is accomplished by the reaction with tetrafluoroboric acid or trifluoromethanesulfonic acid, followed by treatment with base: L. McKinstry, T. Livinghouse, Tetrahedron Lett. 1994, 35, 9319; L. McKinstry, T. Livinghouse, Tetrahedron 1994, 50, 6145.
49. The removal of the boranato group from phosphine-boranes by the use of amines is limited to the compounds bearing aryl groups. Deboranation of trialkylphosphine-boranes is accomplished by the reaction with tetrafluoroboric acid or trifluoromethanesulfonic acid, followed by treatment with base: L. McKinstry, T. Livinghouse, Tetrahedron Lett. 1994, 35, 9319; L. McKinstry, T. Livinghouse, Tetrahedron 1994, 50, 6145.
50. P. K. Freeman, L. L. Hutchinson, J. Org. Chem. 1980, 45, 1924; P. K. Freeman, L. L. Hutchinson, J. Org. Chem. 1983, 48, 4703.
51. P. K. Freeman, L. L. Hutchinson, J. Org. Chem. 1980, 45, 1924; P. K. Freeman, L. L. Hutchinson, J. Org. Chem. 1983, 48, 4703.
52. T. Oshiki, T. Hikosaka, T. Imamoto, Tetrahedron Lett. 1991, 32, 3371; T. Imamoto, T. Oshiki, T. Onozawa, M. Matsuo, T. Hikosaka, M. Yanagawa, Heteroatom Chem. 1992, 3, 563; T. Imamoto, M. Matsuo, T Nonomura, K. Kishikawa, M. Yanagawa, Heteroatom Chem. 1993, 4, 475.
53. T. Oshiki, T. Hikosaka, T. Imamoto, Tetrahedron Lett. 1991, 32, 3371; T. Imamoto, T. Oshiki, T. Onozawa, M. Matsuo, T. Hikosaka, M. Yanagawa, Heteroatom Chem. 1992, 3, 563; T. Imamoto, M. Matsuo, T Nonomura, K. Kishikawa, M. Yanagawa, Heteroatom Chem. 1993, 4, 475.
54. T. Oshiki, T. Hikosaka, T. Imamoto, Tetrahedron Lett. 1991, 32, 3371; T. Imamoto, T. Oshiki, T. Onozawa, M. Matsuo, T. Hikosaka, M. Yanagawa, Heteroatom Chem. 1992, 3, 563; T. Imamoto, M. Matsuo, T Nonomura, K. Kishikawa, M. Yanagawa, Heteroatom Chem. 1993, 4, 475.
55. Yoshikuni and Bailar, Jr. reported that asymmetric hydrogenation of acetamidoacrylic acid catalyzed by a rhodium complex of optically active bis((o-methylphenyl)-phenylphosphino)ethane afforded N-acetylalanine in 49.3% ee: T. Yoshikuni, J. C. Bailar, Jr. Inorg. Chem. 1982, 21, 2129.
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60. R. Kuwano, T. Uemura, M. Saito, Y. Ito, Tetrahedron Lett, 1999, 40, 1327.
61. J. W. Scott, D. D. Keith, G. Nix, Jr., D. R. Parrish, S. Remington, G. P. Roth, J. M. Yownsend, D. Valentine, Jr., R. Yang, J. Org. Chem. 1981, 46, 5086.