Synthesis of a new chiral bisphospholane ligand for the Rh(I)-catalyzed enantioselective hydrogenation of isomeric β-acylamido acrylates

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 1701-1707

  Holz, Jens ^a   Monsees, Axel ^b   Jiao, Haijun ^a   You, Jinsong ^a   Komarov, Igor V ^a   Fischer, Christine ^a   Drauz, Karlheinz ^b   Börner, Armin ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b EVONIK INDUSTRIES AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; HYDROGENATION; SUBSTRATES; SYNTHESIS (CHEMICAL);

LIGANDS;

ACRYLICS;

ACRYLIC ACID DERIVATIVE; ALPHA AMINO ACID; BETA ACYLAMIDOACRYLATE DERIVATIVE; BETA AMINO ACID; MALEIC ANHYDRIDE; PHOSPHINE DERIVATIVE; PHOSPHORUS DERIVATIVE; RHODIUM; SILYLPHOSPHOLANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; HYDROGENATION; ISOMERISM; SYNTHESIS;

EID: 0345314096     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020453h     Document Type: Article

References (67)

1. Sewald, N. In Bioorganic Chemistry, Highlights and New Aspects; Diederichsen, U., Lindhorst, T. K., Westermann, B., Wessjohann, L. A., Eds.; Wiley-VCH: Weinheim, Germany, 1999; Chapter 4.2, p 193. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015.
2. Sewald, N. In Bioorganic Chemistry, Highlights and New Aspects; Diederichsen, U., Lindhorst, T. K., Westermann, B., Wessjohann, L. A., Eds.; Wiley-VCH: Weinheim, Germany, 1999; Chapter 4.2, p 193. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015.
3. Ondetti, M. A.; Engel, S. L. J. Med. Chem. 1975, 18, 761. Stachowiak, K.; Khosla, M. C.; Plucinska, K.; Khairallah, P. A.; Bumpus, F. M. J. Med. Chem. 1979, 22, 1128.
4. Ondetti, M. A.; Engel, S. L. J. Med. Chem. 1975, 18, 761. Stachowiak, K.; Khosla, M. C.; Plucinska, K.; Khairallah, P. A.; Bumpus, F. M. J. Med. Chem. 1979, 22, 1128.
5. For reviews, see: Cole, D. C. Tetrahedron 1994, 50, 9517. Juaristi, E. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997; Sewald, N. Amino Acids 1996, 9, 397. See also: Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341. Saylik, D.; Campi, E. M.; Donohue, A. C.; Jackson, W. R.; Robinson, A. J. Tetrahedron: Asymmetry 2001, 12, 657. Bull, S. D.; Davies, S. G.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2001, 2931.
6. For reviews, see: Cole, D. C. Tetrahedron 1994, 50, 9517. Juaristi, E. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997; Sewald, N. Amino Acids 1996, 9, 397. See also: Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341. Saylik, D.; Campi, E. M.; Donohue, A. C.; Jackson, W. R.; Robinson, A. J. Tetrahedron: Asymmetry 2001, 12, 657. Bull, S. D.; Davies, S. G.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2001, 2931.
7. For reviews, see: Cole, D. C. Tetrahedron 1994, 50, 9517. Juaristi, E. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997; Sewald, N. Amino Acids 1996, 9, 397. See also: Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341. Saylik, D.; Campi, E. M.; Donohue, A. C.; Jackson, W. R.; Robinson, A. J. Tetrahedron: Asymmetry 2001, 12, 657. Bull, S. D.; Davies, S. G.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2001, 2931.
8. For reviews, see: Cole, D. C. Tetrahedron 1994, 50, 9517. Juaristi, E. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997; Sewald, N. Amino Acids 1996, 9, 397. See also: Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341. Saylik, D.; Campi, E. M.; Donohue, A. C.; Jackson, W. R.; Robinson, A. J. Tetrahedron: Asymmetry 2001, 12, 657. Bull, S. D.; Davies, S. G.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2001, 2931.
9. For reviews, see: Cole, D. C. Tetrahedron 1994, 50, 9517. Juaristi, E. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997; Sewald, N. Amino Acids 1996, 9, 397. See also: Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341. Saylik, D.; Campi, E. M.; Donohue, A. C.; Jackson, W. R.; Robinson, A. J. Tetrahedron: Asymmetry 2001, 12, 657. Bull, S. D.; Davies, S. G.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2001, 2931.
10. For reviews, see: Cole, D. C. Tetrahedron 1994, 50, 9517. Juaristi, E. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997; Sewald, N. Amino Acids 1996, 9, 397. See also: Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341. Saylik, D.; Campi, E. M.; Donohue, A. C.; Jackson, W. R.; Robinson, A. J. Tetrahedron: Asymmetry 2001, 12, 657. Bull, S. D.; Davies, S. G.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2001, 2931.
11. (a) Achiwa, K.; Soga, T. Tetrahedron Lett. 1978, 1119.
12. (b) Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543.
13. (c) Zhu, G.; Chen, Z.; Zhang, X. J. Org. Chem. 1999, 64, 6907.
14. (d) Lee, S.-g.; Zhang, Y. J. Org. Lett. 2002, 4, 2429.
15. (e) Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4159.
16. (f) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552.
17. Recently, excellent enantioselectivities were achieved with a chiral Ru-catalyst: Zhou, Y.-G.; Tang, W.; Wang, W.-B.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952.
18. Burk, M. J.; Gross, M. F.; Harper, T. G. P.; Kalberg, C. S.; Lee, J. R.; Martinez, J. P. Pure Appl. Chem. 1996, 68, 37 and references therein.
19. Heller, D.; Holz, J.; Drexler, H.-J.; Lang, J.; Krimmer, H.-P.; Drauz, K.; Börner, A. J. Org. Chem. 2001, 66, 6816. Heller, D.; Drexler, H.-J.; You, J.; Drauz, K.; Krimmer, H.-P.; Börner, A. Chem. Eur. J. 2002, 8, 5196.
20. Heller, D.; Holz, J.; Drexler, H.-J.; Lang, J.; Krimmer, H.-P.; Drauz, K.; Börner, A. J. Org. Chem. 2001, 66, 6816. Heller, D.; Drexler, H.-J.; You, J.; Drauz, K.; Krimmer, H.-P.; Börner, A. Chem. Eur. J. 2002, 8, 5196.
21. Holz, J.; Stürmer, R.; Schmidt, U.; Drexler, H.-J.; Heller, D.; Krimmer, H.-P.; Börner, A. Eur. J. Org. Chem. 2001, 4615.
22. Dierkes, P.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1999, 1519.
23. Fernandez, E.; Gillon, A.; Heslop, K.; Horwood, E.; Hyett, D. J.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 1663.
24. (a) Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.
25. (b) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlowe, R. L. J. Am. Chem. Soc. 1993, 115, 10125.
26. (a) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653.
27. (b) Burk, M. J.; Harlow, R. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1462.
28. (c) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569.
29. (a) Achiral bisphospholanes: Field, L. D.; Thomas, I. P. Inorg. Chem. 1996, 35, 2546.
30. (b) Chiral bisphospholanes: (1) Nonfunctionalized: Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363. Dierkes, P.; Ramdeehul, S.; Barloy, L.; De Cian, A.; Fischer, J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Osborn, J. A. Angew. Chem., Int. Ed. 1998, 37, 3116.
31. (b) Chiral bisphospholanes: (1) Nonfunctionalized: Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363. Dierkes, P.; Ramdeehul, S.; Barloy, L.; De Cian, A.; Fischer, J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Osborn, J. A. Angew. Chem., Int. Ed. 1998, 37, 3116.
32. Functionalized: Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031. Carmichael, D.; Doucet, H.; Brown, J. M. Chem. Commun. 1999, 261. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701. Yan, Y.-Y.; RajanBabu, T. V. J. Org. Chem. 2000, 65, 900. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489.
33. Functionalized: Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031. Carmichael, D.; Doucet, H.; Brown, J. M. Chem. Commun. 1999, 261. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701. Yan, Y.-Y.; RajanBabu, T. V. J. Org. Chem. 2000, 65, 900. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489.
34. Functionalized: Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031. Carmichael, D.; Doucet, H.; Brown, J. M. Chem. Commun. 1999, 261. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701. Yan, Y.-Y.; RajanBabu, T. V. J. Org. Chem. 2000, 65, 900. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489.
35. Functionalized: Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031. Carmichael, D.; Doucet, H.; Brown, J. M. Chem. Commun. 1999, 261. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701. Yan, Y.-Y.; RajanBabu, T. V. J. Org. Chem. 2000, 65, 900. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489.
36. Functionalized: Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031. Carmichael, D.; Doucet, H.; Brown, J. M. Chem. Commun. 1999, 261. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701. Yan, Y.-Y.; RajanBabu, T. V. J. Org. Chem. 2000, 65, 900. Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489.
37. 4. Marinetti, A.; Genêt, J. P.; Jus, S.; Blanc, D.; Ratovelomanana-Vidal, V. Chem. Eur. J. 1999, 5, 1160. Berens, U.; Burk, M. J.; Gerlach, A.; Hems, W. Angew. Chem., Int. Ed. 2000, 39, 1981. Marinetti, A.; Carmichael, D. Chem. Rev. 2002, 102, 201.
38. 4. Marinetti, A.; Genêt, J. P.; Jus, S.; Blanc, D.; Ratovelomanana-Vidal, V. Chem. Eur. J. 1999, 5, 1160. Berens, U.; Burk, M. J.; Gerlach, A.; Hems, W. Angew. Chem., Int. Ed. 2000, 39, 1981. Marinetti, A.; Carmichael, D. Chem. Rev. 2002, 102, 201.
39. 4. Marinetti, A.; Genêt, J. P.; Jus, S.; Blanc, D.; Ratovelomanana-Vidal, V. Chem. Eur. J. 1999, 5, 1160. Berens, U.; Burk, M. J.; Gerlach, A.; Hems, W. Angew. Chem., Int. Ed. 2000, 39, 1981. Marinetti, A.; Carmichael, D. Chem. Rev. 2002, 102, 201.
40. Burk, M. J.; Pizzano, A.; Martin, J. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 2000, 19, 250.
41. Low yields might be due to the reaction of the very reactive Li-phosphide 5 with THF used as a solvent and its propensity to engage in electron-transfer processes (ref 12).
42. Morimoto, T.; Ando, N.; Achiwa, K. Synlett 1996, 1211.
43. Schmidbaur, H.; Paschalidis, C.; Steigelmann, O.; Wilkinson, D. L.; Müller, G. Chem. Ber. 1989, 122, 1857. Marinetti, A.; Kruger, V.; Buzin, F. X. Tetrahedron Lett. 1997, 38, 2947. Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391.
44. Schmidbaur, H.; Paschalidis, C.; Steigelmann, O.; Wilkinson, D. L.; Müller, G. Chem. Ber. 1989, 122, 1857. Marinetti, A.; Kruger, V.; Buzin, F. X. Tetrahedron Lett. 1997, 38, 2947. Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391.
45. Schmidbaur, H.; Paschalidis, C.; Steigelmann, O.; Wilkinson, D. L.; Müller, G. Chem. Ber. 1989, 122, 1857. Marinetti, A.; Kruger, V.; Buzin, F. X. Tetrahedron Lett. 1997, 38, 2947. Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391.
46. Becher, H.-J.; Fenske, D.; Langer, E. Chem. Ber. 1973, 106, 177. Fenske, D.; Becher, H.-J. Chem. Ber. 1974, 107, 117. Fenske, D.; Becher, H.-J. Chem. Ber. 1975, 108, 245. Becher, H.-J.; Fenske, D.; Langer, E.; Prokscha, H. Monatshefte Chem. 1980, 111, 749. Kinting, A.; Krause, H.-W. J. Organomet. Chem. 1986, 302, 259. Kinting, A.; Döbler, C. J. Organomet. Chem. 1989, 370, 351. Tillack, A.; Michalik, M.; Fenske, D.; Goesmann, H. J. Organomet. Chem. 1993, 454, 95. For a review concerned with the synthesis and properties of silylphosphines, see: Fritz, G.; Scheer, P. Chem. Rev. 2000, 101, 3341.
47. Becher, H.-J.; Fenske, D.; Langer, E. Chem. Ber. 1973, 106, 177. Fenske, D.; Becher, H.-J. Chem. Ber. 1974, 107, 117. Fenske, D.; Becher, H.-J. Chem. Ber. 1975, 108, 245. Becher, H.-J.; Fenske, D.; Langer, E.; Prokscha, H. Monatshefte Chem. 1980, 111, 749. Kinting, A.; Krause, H.-W. J. Organomet. Chem. 1986, 302, 259. Kinting, A.; Döbler, C. J. Organomet. Chem. 1989, 370, 351. Tillack, A.; Michalik, M.; Fenske, D.; Goesmann, H. J. Organomet. Chem. 1993, 454, 95. For a review concerned with the synthesis and properties of silylphosphines, see: Fritz, G.; Scheer, P. Chem. Rev. 2000, 101, 3341.
48. Becher, H.-J.; Fenske, D.; Langer, E. Chem. Ber. 1973, 106, 177. Fenske, D.; Becher, H.-J. Chem. Ber. 1974, 107, 117. Fenske, D.; Becher, H.-J. Chem. Ber. 1975, 108, 245. Becher, H.-J.; Fenske, D.; Langer, E.; Prokscha, H. Monatshefte Chem. 1980, 111, 749. Kinting, A.; Krause, H.-W. J. Organomet. Chem. 1986, 302, 259. Kinting, A.; Döbler, C. J. Organomet. Chem. 1989, 370, 351. Tillack, A.; Michalik, M.; Fenske, D.; Goesmann, H. J. Organomet. Chem. 1993, 454, 95. For a review concerned with the synthesis and properties of silylphosphines, see: Fritz, G.; Scheer, P. Chem. Rev. 2000, 101, 3341.
49. Becher, H.-J.; Fenske, D.; Langer, E. Chem. Ber. 1973, 106, 177. Fenske, D.; Becher, H.-J. Chem. Ber. 1974, 107, 117. Fenske, D.; Becher, H.-J. Chem. Ber. 1975, 108, 245. Becher, H.-J.; Fenske, D.; Langer, E.; Prokscha, H. Monatshefte Chem. 1980, 111, 749. Kinting, A.; Krause, H.-W. J. Organomet. Chem. 1986, 302, 259. Kinting, A.; Döbler, C. J. Organomet. Chem. 1989, 370, 351. Tillack, A.; Michalik, M.; Fenske, D.; Goesmann, H. J. Organomet. Chem. 1993, 454, 95. For a review concerned with the synthesis and properties of silylphosphines, see: Fritz, G.; Scheer, P. Chem. Rev. 2000, 101, 3341.
50. Becher, H.-J.; Fenske, D.; Langer, E. Chem. Ber. 1973, 106, 177. Fenske, D.; Becher, H.-J. Chem. Ber. 1974, 107, 117. Fenske, D.; Becher, H.-J. Chem. Ber. 1975, 108, 245. Becher, H.-J.; Fenske, D.; Langer, E.; Prokscha, H. Monatshefte Chem. 1980, 111, 749. Kinting, A.; Krause, H.-W. J. Organomet. Chem. 1986, 302, 259. Kinting, A.; Döbler, C. J. Organomet. Chem. 1989, 370, 351. Tillack, A.; Michalik, M.; Fenske, D.; Goesmann, H. J. Organomet. Chem. 1993, 454, 95. For a review concerned with the synthesis and properties of silylphosphines, see: Fritz, G.; Scheer, P. Chem. Rev. 2000, 101, 3341.
51. Becher, H.-J.; Fenske, D.; Langer, E. Chem. Ber. 1973, 106, 177. Fenske, D.; Becher, H.-J. Chem. Ber. 1974, 107, 117. Fenske, D.; Becher, H.-J. Chem. Ber. 1975, 108, 245. Becher, H.-J.; Fenske, D.; Langer, E.; Prokscha, H. Monatshefte Chem. 1980, 111, 749. Kinting, A.; Krause, H.-W. J. Organomet. Chem. 1986, 302, 259. Kinting, A.; Döbler, C. J. Organomet. Chem. 1989, 370, 351. Tillack, A.; Michalik, M.; Fenske, D.; Goesmann, H. J. Organomet. Chem. 1993, 454, 95. For a review concerned with the synthesis and properties of silylphosphines, see: Fritz, G.; Scheer, P. Chem. Rev. 2000, 101, 3341.
52. Becher, H.-J.; Fenske, D.; Langer, E. Chem. Ber. 1973, 106, 177. Fenske, D.; Becher, H.-J. Chem. Ber. 1974, 107, 117. Fenske, D.; Becher, H.-J. Chem. Ber. 1975, 108, 245. Becher, H.-J.; Fenske, D.; Langer, E.; Prokscha, H. Monatshefte Chem. 1980, 111, 749. Kinting, A.; Krause, H.-W. J. Organomet. Chem. 1986, 302, 259. Kinting, A.; Döbler, C. J. Organomet. Chem. 1989, 370, 351. Tillack, A.; Michalik, M.; Fenske, D.; Goesmann, H. J. Organomet. Chem. 1993, 454, 95. For a review concerned with the synthesis and properties of silylphosphines, see: Fritz, G.; Scheer, P. Chem. Rev. 2000, 101, 3341.
53. Becher, H.-J.; Fenske, D.; Langer, E. Chem. Ber. 1973, 106, 177. Fenske, D.; Becher, H.-J. Chem. Ber. 1974, 107, 117. Fenske, D.; Becher, H.-J. Chem. Ber. 1975, 108, 245. Becher, H.-J.; Fenske, D.; Langer, E.; Prokscha, H. Monatshefte Chem. 1980, 111, 749. Kinting, A.; Krause, H.-W. J. Organomet. Chem. 1986, 302, 259. Kinting, A.; Döbler, C. J. Organomet. Chem. 1989, 370, 351. Tillack, A.; Michalik, M.; Fenske, D.; Goesmann, H. J. Organomet. Chem. 1993, 454, 95. For a review concerned with the synthesis and properties of silylphosphines, see: Fritz, G.; Scheer, P. Chem. Rev. 2000, 101, 3341.
54. Fiaud, J.-C.; Legros, J.-Y. Tetrahedron Lett. 1991, 32, 5089. Guillen, F.; Moinet, C.; Fiaud, J.-C. Bull. Soc. Chim. Fr. 1997, 143, 371. Hume, S. C.; Simpkins, N. S. J. Org. Chem. 1998, 63, 912. Guillen, F.; Fiaud, J.-C. Tetrahedron Lett. 1999, 40, 2939.
55. Fiaud, J.-C.; Legros, J.-Y. Tetrahedron Lett. 1991, 32, 5089. Guillen, F.; Moinet, C.; Fiaud, J.-C. Bull. Soc. Chim. Fr. 1997, 143, 371. Hume, S. C.; Simpkins, N. S. J. Org. Chem. 1998, 63, 912. Guillen, F.; Fiaud, J.-C. Tetrahedron Lett. 1999, 40, 2939.
56. Fiaud, J.-C.; Legros, J.-Y. Tetrahedron Lett. 1991, 32, 5089. Guillen, F.; Moinet, C.; Fiaud, J.-C. Bull. Soc. Chim. Fr. 1997, 143, 371. Hume, S. C.; Simpkins, N. S. J. Org. Chem. 1998, 63, 912. Guillen, F.; Fiaud, J.-C. Tetrahedron Lett. 1999, 40, 2939.
57. Fiaud, J.-C.; Legros, J.-Y. Tetrahedron Lett. 1991, 32, 5089. Guillen, F.; Moinet, C.; Fiaud, J.-C. Bull. Soc. Chim. Fr. 1997, 143, 371. Hume, S. C.; Simpkins, N. S. J. Org. Chem. 1998, 63, 912. Guillen, F.; Fiaud, J.-C. Tetrahedron Lett. 1999, 40, 2939.
58. 4 precatalyst for the enantioselective hydrogenation of methyl -N-acetamido cinnamate in MeOH, 94.0% ee was achieved.
59. . Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.1; Gaussian, Inc.: Pittsburgh, PA, 1998.
60. 6.
61. +, 82.8°. Exo PC=C angles: 1, 124.5°; Me-DuPHOS, 120.3°.
62. Popova, E. V.; Patsanovskii, I. I.; Livantsov, M. V.; Ishmaeva, E. A. Russ. J. Gen. Chem. 1996, 66, 1369; Zh. Obshch. Khim. 1996, 66, 1369.
63. Popova, E. V.; Patsanovskii, I. I.; Livantsov, M. V.; Ishmaeva, E. A. Russ. J. Gen. Chem. 1996, 66, 1369; Zh. Obshch. Khim. 1996, 66, 1369.
64. Shabana, R.; Rasmussen, J. B.; Lawesson, S.-O. Bull. Soc. Chim. Belg. 1981, 90, 75. Yakimovich, S. I.; Kajukova, L. A.; Chrustaljev, W. A.; Zazenkina, L. A. J. Org. Chem. USSR 1977, 13, 1069; Zh. Org. Khim. 1977, 13, 1161. Grob, C. A. Helv. Chim. Acta 1950, 33, 1787.
65. Shabana, R.; Rasmussen, J. B.; Lawesson, S.-O. Bull. Soc. Chim. Belg. 1981, 90, 75. Yakimovich, S. I.; Kajukova, L. A.; Chrustaljev, W. A.; Zazenkina, L. A. J. Org. Chem. USSR 1977, 13, 1069; Zh. Org. Khim. 1977, 13, 1161. Grob, C. A. Helv. Chim. Acta 1950, 33, 1787.
66. Shabana, R.; Rasmussen, J. B.; Lawesson, S.-O. Bull. Soc. Chim. Belg. 1981, 90, 75. Yakimovich, S. I.; Kajukova, L. A.; Chrustaljev, W. A.; Zazenkina, L. A. J. Org. Chem. USSR 1977, 13, 1069; Zh. Org. Khim. 1977, 13, 1161. Grob, C. A. Helv. Chim. Acta 1950, 33, 1787.
67. Shabana, R.; Rasmussen, J. B.; Lawesson, S.-O. Bull. Soc. Chim. Belg. 1981, 90, 75. Yakimovich, S. I.; Kajukova, L. A.; Chrustaljev, W. A.; Zazenkina, L. A. J. Org. Chem. USSR 1977, 13, 1069; Zh. Org. Khim. 1977, 13, 1161. Grob, C. A. Helv. Chim. Acta 1950, 33, 1787.