Reversed stereochemical control in the presence of CeCl3 and TiCl4 in the Lewis acid mediated reduction of α-alkyl-β-keto esters by metal hydrides. A general methodology for the diastereoselective synthesis of syn- and anti-α-alkyl-β-hydroxy esters

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 1986-1992

  Marcantoni, Enrico ^a   Alessandrini, Sara ^a   Malavolta, Marco ^a   Bartoli, Giuseppe ^b   Bellucci, Maria Cristina ^b   Sambri, Letizia ^b   Dalpozzo, Renato ^c  

^a Dipartimento di Scienze Chimiche dell'Universita   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF CALABRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; METAL; REDUCING AGENT;

ARTICLE; CHELATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; ISOMER; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033582984     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9821574     Document Type: Article

References (69)

1. Greeves, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 1-24.
2. Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338.
3. (a) Sato, T.; Nishio, M.; Otera, J. Synlett 1995, 965.
4. (b)Taniguchi, M.; Fujii, H.; Oshima, K.; Utimoto, K. Tetrahedron 1993, 49, 11169.
5. (c) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5405.
6. (d) Fujita, M.; Hiyama, T. J. Am. Chem. Soc. 1985, 107, 8294.
7. (e) Ito, Y.; Yamaguchi, M. Tetrahedron Lett. 1982, 24, 5385.
8. (f) Sorrell, T. N.; Pearlman, P. S. Tetrahedron Lett. 1980, 21, 3963.
9. (a) Dauchet, S.; Bigot, C.; Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1997, 8, 1735.
10. (b) Shieh, W.-R.; Sih, C. J. Tetrahedron: Asymmetry 1993, 4, 1259.
11. (c) Jian-Xiu, G.; Gno-Qiang, L. Tetrahedron 1993, 49, 5805.
12. (d) Servi, S. Synthesis 1990, 1.
13. (e) Nakamura, K.; Miyai, T.; Nagar, A.; Oka, S.; Ohno, A. Bull. Chem. Soc. Jpn. 1989, 62, 1179.
14. Bartlett, P. A. Tetrahedron 1980, 36, 3.
15. (a) Shirai, F.; Nakai, T. Chem. Lett. 1989, 445.
16. (b) Wild, H.; Kant, J.; Walker, D. G.; Ojima, I.; Ternansky, R. J.; Morin, J. M., Jr.; Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; and references therein.
17. (a) Mead, K. T.; Park, M. Tetrahedron Lett. 1995, 36, 1205.
18. (b) Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365.
19. (c) Hanessian, S.; Tehim, A.; Chen, P. J. Org. Chem. 1993, 58, 7768.
20. (d) Thompson, K. L.; Chang, M. N.; Chiang, Y.-C. P.; Yang, S. S.; Chabala, J. C.; Arison, B. H.; Greenspan, M. D.; Hauf, D. P.; Yudkovitz, J. Tetrahedron Lett. 1991, 32, 3337.
21. (e) Chiang, Y. P.; Yang, S. S.; Heck, J. V.; Chabala, J. C.; Chang, M. N. J. Org. Chem. 1989, 54, 5708.
22. (f) Marshall, J. A.; Lebreton, J. J. Am. Chem. Soc. 1988, 110, 2925.
23. (a) Bal, B.; Buse, C. T.; Smith, K.; Heathcock, C. H. Org. Synth. 1985, 63, 89.
24. (b) Montgomery, S. H.; Pirrung, M. C.; Heathcock, C. H. Org. Synth. 1985, 63, 99.
25. (c) Meyers. A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309.
26. (d) Heathcock, C. H.; Pirrung, M. C.; Montgomery, S. H.; Lampe, J. Tetrahedron 1981, 37, 4087.
27. (a) Bartoli, G.; Bosco, M.; Cingolani, S.; Marcantoni, E.; Sambri, L. J. Org. Chem. 1998, 63, 3624.
28. (b) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem. Eur. J. 1997, 3, 1941.
29. (c) Bartoli, G.; Bosco, M.; Marcantoni, E.; Sambri, L. Tetrahedron Lett. 1996, 35, 241.
30. Sweeney, J. B. In Comprehensive Organic Functional Group Transformation; Katritzky, A. R., Meth-cohn, O., Rees, C. W., Eds.; Elsevier Science Ltd.: Oxford, 1995; Vol. 2, pp 52-82.
31. (a) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: London, 1988.
32. (b) Lane, C. F. Aldrichim. Acta 1973, 6, 51.
33. Nakata, T.; Oishi, T. Tetrahedron Lett. 1980, 21, 1641.
34. Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868.
35. Reviews on chelation-and nonchelation-controlled additions: (a) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
36. (b) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462.
37. (c) Jonas, V.; Frenking, G.; Reetz, M. T. Organometallics 1993, 12, 2110.
38. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; John Wiley & Sons: Chichester, 1994; pp 195-282.
39. Hubert-Pfalzgraf, L. G.; Machado, L.; Vaissermann, J. Polyhedron 1996, 15, 546.
40. (a) Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
41. (b) Anh, N. T.; Einsenstein, O. Nouv. J. Chim. 1977, 1, 61.
42. (a) Bürgi, H. B.; Dunitz, J. D.; Shefter, E. J. J. Am. Chem. Soc. 1973, 95, 5065.
43. (b) Bürgi, H. B.; Dunitz, J. D.; Lehn, J. M.; Wipff, G. Tetrahedron 1974, 30, 1563.
44. Bürgi, H. B.; Lehn, J. M.; Wipff, G. J. Am. Chem. Soc. 1974, 96, 1956.
45. The water molecule found in dry cerium(III) chloride seems to have no effect, since the material was highly efficient without a large excess of reducing agent. cf. Evans, W. J.; Feldaman, J. D.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 4581.
46. Greeves, N.; Pease, J. E.; Bowden, M. C.; Brown, S. M. Tetrahedron Lett. 1996, 37, 2675.
47. 1H NMR spectrum was measured after warming to -78°C, it was referenced to residual tetrahydrofuran (δ 3.58 ppm, δ 1.73 ppm), and a broad new peak did not appear.
48. Fukuzawa, S.; Fujinami, T.; Yamanchi, S.; Sakai, S. J. Chem. Soc., Perkin Trans. 1 1986, 1929.
49. Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1985, 26, 4643.
50. Brown, H. C.; Kim, S. C.; Krishnamurthy, S. J. Org. Chem. 1980, 45, 1.
51. Bartoli, G.; Bosco, M.; Marcantoni, E.; Sambri, L. Tetrahedron Lett. 1996, 37, 7421.
52. House, H. O.; Crumrine, D. S.; Teramishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310.
53. (a) Frater, G.; Müller, U.; Günther, W. Tetrahedron 1984, 40, 1277.
54. (b) Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, T. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066.
55. (c) Mulzer, J.; Zippel, M.; Brumtrup, G.; Segner, J.; Finke, J. Liebigs Ann. Chem. 1980, 1108.
56. (d) Heathcock, C. H.; Pirrung, M. C.; Sohn, J. E. J. Org. Chem. 1979, 44, 4294.
57. Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997.
58. (a) Arjona, O.; Pérez-Ossorio, R.; Pérez-Rubalcaba, A.; Quiroga, M. L. J. Chem. Soc., Perkin Trans. 2 1981, 597.
59. (b) Alvarez-Ibarra, C.; Arjona-Loraque, O.; Pérez-Rubalcaba, A.; Plumet, J. Rev. R. Acad. Cienc. Exactas, Fis. Nat. Madrid 1979, 73.
60. Armarego, W. L. F.; Perrin, D. D. In Purification of Laboratory Chemicals, 4th ed.; Butterworth Heinemann: Oxford, 1996.
61. Martin, V. A.; Murray, D. H.; Pratt, N. E.; Zhao, Y.; Albizati, K. F. J. Am. Chem. Soc. 1990, 112, 6965.
62. Queignes, R; Kirschleger, B.; Lambert, F.; Aboutaj, M. Synth. Commun. 1998, 18, 1213.
63. (a) Kim, H.-O.; Carrol, B.; Lee, M. S. Synth. Commun. 1997, 27, 2505.
64. (b) Reynolds, R. C.; Trask, T. W.; Sedwick, W. D. J. Org. Chem. 1991, 56, 2391.
65. Bartoli, G.; Bosco, M.; Bellucci, M. C.; Marcantoni, E.; Sambri, L.; Torregiani, E. Eur. J. Org. Chem. 1999, 617.
66. Reetz, M. T.; Chatziiosifidis, I.; Hubner, F.; Heimbach, H. Org. React. 1984, 31, 101.
67. Turner, J. A.; Jacks, W. S. J. Org. Chem. 1989, 54, 4229.
68. Descriptors R*,S* indicate that diastereomeric compounds are obtained as racemates. We prefer this terminology to avoid the ambiguities that could arise from syn-anti descriptors.
69. Imamoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 231-250.