Enantioselective Methods for Chiral Cyclohexane Ring Synthesis

Accounts of Chemical Research

Volumn 23, Issue 7, 1990, Pages 207-213

  Schultz, Arthur G ^a  

^a RENSSELAER POLYTECHNIC INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000908715     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar00175a001     Document Type: Article

References (47)

1. Schultz, A. G. Acc. Chem. Res. 1983, 16, 210.
2. Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1984; Vol. 3, pp 1–110.
3. For recent syntheses of enantiomerically pure cyclohexane derivatives, see: Herradon, B.; Seebach, D. Helv. Chim. Acta 1989, 72, 690 and references cited therein.
4. For interesting insight to “the origin of the Birch reduction”, see: Birch, A. J. J. Chem. Educ. 1975, 52, 458.
5. Wooster, C. B. (to E. I. du Pont de Nemours and Co.) U.S. Patent 2, 182, 242; Chem. Abstr. 1940, 34, 1993.
6. For reviews of alkali metal in ammonia reduction and reductive alkylation of aromatic compounds, see: Hook, J. M.; Mander, L. N. Nat. Prod. Rep. 1986, 3, 35 and references cited therein.
7. Marshall, J. A.; Wuts, P. G. M. J. Org. Chem. 1978, 43, 1086.
8. Marshall, J. A.; Wuts, P. G. M. J. Org. Chem. 1977, 42, 1794.
9. Yamada, K.; Nagase, H.; Hayakawa, Y.; Aoki, K.; Hirata, Y. Tetrahedron Lett. 1973, 4963.
10. Zutterman, F.; de Wilde, H.; Mijngheer, R.; de Clercq, P.; Vandewalle, M. Tetrahedron 1979, 35, 2389.
11. For a related route that begins by the Birch reduction of p-methoxybenzyl alcohol, see: Isobe, M.; Iio, H.; Kawai, T.; Goto, T. J. Am. Chem. Soc. 1978, 100, 1940.
12. For a discussion of the use of L-prolinol in asymmetric synthesis, see: Enders, D.; Kipphardt, H. Nachr. Chem., Tech. Lab 1985, 33, 882.
13. Schultz, A. G.; Macielag, M.; Sundararaman, P.; Taveras, A. G.; Welch, M. J. Am. Chem. Soc. 1988, 110, 7828.
14. Schultz, A. G.; Puig, S. J. Org. Chem. 1985, 50, 915.
15. Reduction of N N-dialkylbenzamides with lithium can sometimes result in significant carbonyl group reduction. Functional-group reduction usually can be avoided by utilization of potassium metal; if the lithium enolate is required, then exchange with LiBr is recommended. For an investigation of the reaction parameters for Birch reduction and reductive alkylation of benzonitriles and benzamides, see: Schultz, A. G.; Macielag, M. J. Org. Chem. 1986, 51, 4983.
16. McCloskey, P. J.; Schultz, A. G. Heterocycles 1987, 25, 437.
17. Green, N., unpublished results, For a review of benzylic substitutions directed by a tertiary amide, see: Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306.
18. For an example of impressive solvent effects in the asymmetric alkylations of chiral metalloenamines prepared from β-keto esters, see: Tomioka, K.; Ando, K.; Takemaso, Y.; Koga, K. J. Am. Chem. Soc. 1984, 106, 2718.
19. Tomioka, K.; Yasuda, K.; Koga, K. J. Chem. Soc, Chem. Commun. 1987, 1345.
20. Birch reductions of 2- and 4-biphenylcarboxylic acids have been reported to give dihydrobenzoic acids: Franks, D.; Grossei, M. C.; Hayward, R. C.; Knutsen, L. J. S. J. Chem. Soc, Chem. Commun. 1978, 941.
21. Rabideau, P. W.; Nyikos, S. J.; Huser, D. L.; Burkholder, E. G. J. Chem. Soc, Chem. Commun. 1980, 210.
22. Schultz, A. G.; Macielag, M.; Podhorez, D. E.; Suhadolnik, J. C.; Kullnig, R. K. J. Org. Chem. 1988, 53, 2456.
23. 2C-0 bond cleavage at C(4) during Birch reduction. For a discussion of related hydrogenolysis reactions, see: Keefer, L. K.; Lunn, G. Chem. Rev. 1989, 89, 459.
24. Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K. Heterocycles 1979, 12, 1475.
25. Schultz, A. G.; McCloskey, P.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493.
26. Schultz, A. G.; Sundararaman, P. Tetrahedron Lett. 1984, 25, 4591.
27. Crabtree, R. H.; Felkin, H.; Fellebeen-Khan, T.; Morris, G. E. J. Organomet. Chem. 1979, 168, 183.
28. Schultz, A. G.; McCloskey, P. J. J. Org. Chem. 1985, 50, 5905.
29. McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380.
30. Schultz, A. G.; Dittami, J. P. Tetrahedron Lett. 1983, 24, 1369.
31. Schultz, A. G.; Dittami, J. P.; Lavieri, F. P.; Salowey, C.; Sundararaman, P.; Szymula, M. B. J. Org. Chem. 1984, 49, 4429.
32. Schultz, A. G.; Lavieri, F. P.; Macielag, M. Tetrahedron Lett. 1986, 27, 1481.
33. Schultz, A. G.; Taveras, A. G.; Harrington, R. E. Tetrahedron Lett. 1988, 29, 3907.
34. For a review of the chemistry of cyclohexadienones, see: Waring, A. J. In Advances in Alicyclic Chemistry; Hart, H., Karabatsos, G. J., Eds.; Academic Press: New York, 1966; Vol. 1, p 129.
35. Schultz, A. G.; Lavieri, F. P.; Snead, T. E. J. Org. Chem. 1985, 50, 3086.
36. For a review of relevant work in this area, see: Schultz, A. G. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1988; Vol. 1, p 53.
37. Schultz, A. G.; Eng, K. K. Tetrahedron Lett. 1986, 27, 2331.
38. Schultz, A. G., Staib, R. R.; Eng, K. K. J. Org. Chem. 1987, 52, 2968.
39. Barton, D. H. R.; Quinkert, G. J. Chem. Soc. 1960, 1.
40. Schultz, A. G.; Sundararaman, P.; Macielag, M.; Lavieri, F. P.; Welch, M. Tetrahedron Lett. 1985, 26, 4575.
41. Lavieri, F. P. Ph.D. Thesis, Rensselaer Polytechnic Institute, 1986.
42. Schultz, A. G.; Lavieri, F. P.; Macielag, M.; Plummer, M. J. Am. Chem. Soc. 1987, 109, 3991.
43. Schultz, A. G.; Plummer, M.; Taveras, A. G.; Kullnig, R. K. J. Chem. Soc. 1988, 110, 5547.
44. Schultz, A. G.; Geisa, W.; Kullnig, R. K. J. Org. Chem. 1989, 54, 3158.
45. Schultz, A. G.; Macielag, M.; Plummer, M. J. Org.Chem. 1988, 53, 391.
46. Schultz, A. G.; Plummer, M. J. Org. Chem. 1989, 54, 2112.
47. Schultz, A. G. Pure Appl. Chem. 1988, 60, 981.