Stereocontrolled functionalization in acyclic systems by exploiting internal 1,2-asymmetric induction - Generation of polypropionate and related motifs

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7473-7476

  Hanessian, Stephen ^a   Gai, Yonghua ^a   Wang, Wengui ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; HYDROXYACID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030583463     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01753-4     Document Type: Article

References (44)

1. 1. For some authoritative monographs, see Nicolaou, K.C., Sorensen, E.J. in Classics in Total Synthesis, VCH Publishers, New York, N.Y., 1996; Corey, E.J.; Cheng, X.M. The Logic of Chemical Synthesis, Wiley, N.Y. 1989; The Total Synthesis of Natural Products, ApSimon, J. Ed., Wiley, N.Y., vol. 1-8 1973-1992; Studies in Natural Product Synthesis, Atta-ur-Rahman ed. Elsevier, Amsterdam, vol. 1-13 (1988-1994); Strategies and Tactics in Organic Synthesis, Lindberg, T. Ed., Academic, San Diego, Ca., vol. 1-3, 1984-1993.
2. 1. For some authoritative monographs, see Nicolaou, K.C., Sorensen, E.J. in Classics in Total Synthesis, VCH Publishers, New York, N.Y., 1996; Corey, E.J.; Cheng, X.M. The Logic of Chemical Synthesis, Wiley, N.Y. 1989; The Total Synthesis of Natural Products, ApSimon, J. Ed., Wiley, N.Y., vol. 1-8 1973-1992; Studies in Natural Product Synthesis, Atta-ur-Rahman ed. Elsevier, Amsterdam, vol. 1-13 (1988-1994); Strategies and Tactics in Organic Synthesis, Lindberg, T. Ed., Academic, San Diego, Ca., vol. 1-3, 1984-1993.
3. 1. For some authoritative monographs, see Nicolaou, K.C., Sorensen, E.J. in Classics in Total Synthesis, VCH Publishers, New York, N.Y., 1996; Corey, E.J.; Cheng, X.M. The Logic of Chemical Synthesis, Wiley, N.Y. 1989; The Total Synthesis of Natural Products, ApSimon, J. Ed., Wiley, N.Y., vol. 1-8 1973-1992; Studies in Natural Product Synthesis, Atta-ur-Rahman ed. Elsevier, Amsterdam, vol. 1-13 (1988-1994); Strategies and Tactics in Organic Synthesis, Lindberg, T. Ed., Academic, San Diego, Ca., vol. 1-3, 1984-1993.
4. 1. For some authoritative monographs, see Nicolaou, K.C., Sorensen, E.J. in Classics in Total Synthesis, VCH Publishers, New York, N.Y., 1996; Corey, E.J.; Cheng, X.M. The Logic of Chemical Synthesis, Wiley, N.Y. 1989; The Total Synthesis of Natural Products, ApSimon, J. Ed., Wiley, N.Y., vol. 1-8 1973-1992; Studies in Natural Product Synthesis, Atta-ur-Rahman ed. Elsevier, Amsterdam, vol. 1-13 (1988-1994); Strategies and Tactics in Organic Synthesis, Lindberg, T. Ed., Academic, San Diego, Ca., vol. 1-3, 1984-1993.
5. 1. For some authoritative monographs, see Nicolaou, K.C., Sorensen, E.J. in Classics in Total Synthesis, VCH Publishers, New York, N.Y., 1996; Corey, E.J.; Cheng, X.M. The Logic of Chemical Synthesis, Wiley, N.Y. 1989; The Total Synthesis of Natural Products, ApSimon, J. Ed., Wiley, N.Y., vol. 1-8 1973-1992; Studies in Natural Product Synthesis, Atta-ur-Rahman ed. Elsevier, Amsterdam, vol. 1-13 (1988-1994); Strategies and Tactics in Organic Synthesis, Lindberg, T. Ed., Academic, San Diego, Ca., vol. 1-3, 1984-1993.
6. 2. See for example Collins, A.N.; Sheldrake, G.N.; Crosby, J., Chirality in Industry, J. Wiley & Sons New York, N.Y. (1992); Sheldon, R.A. Chirotechnology. Industrial Synthesis of Optically Acitive Compounds, , M. Dekker, Inc. New York, NY (1993).
7. 2. See for example Collins, A.N.; Sheldrake, G.N.; Crosby, J., Chirality in Industry, J. Wiley & Sons New York, N.Y. (1992); Sheldon, R.A. Chirotechnology. Industrial Synthesis of Optically Acitive Compounds, , M. Dekker, Inc. New York, NY (1993).
8. 3. For excellent recent reviews, see a. Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555; b. Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 51, 8135; c. Lowe, G. Chem. Soc. Rev. 1995, 309.
9. 3. For excellent recent reviews, see a. Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555; b. Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 51, 8135; c. Lowe, G. Chem. Soc. Rev. 1995, 309.
10. 3. For excellent recent reviews, see a. Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555; b. Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 51, 8135; c. Lowe, G. Chem. Soc. Rev. 1995, 309.
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13. 5. For representative methdology and a historical perspective, see Roush, W.R.; Palkowitz, A.D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348; Hanessian, S. Aldrichimica Acta 1989, 22, 3; Stork, G.; Rychnovsky, S. Pure Appl. Chem. 1986, 55, 767; Heathcock, C.H. in Asymmetric Synthesis, Morrison, J.D., Ed. Academic, Orlando, Fla., 1984; Evans, D.A. Aldrichimica Acta 1982, 15, 23; Masamune, S.; Choy, W. Aldrichimica Acta 1982, 15, 47; Still, W.C.; Barrish, J.C. J. Am. Chem. Soc. 1983, 105, 2487; Mukaiyama, T. Org. React. 1982, 28, 103.
14. 5. For representative methdology and a historical perspective, see Roush, W.R.; Palkowitz, A.D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348; Hanessian, S. Aldrichimica Acta 1989, 22, 3; Stork, G.; Rychnovsky, S. Pure Appl. Chem. 1986, 55, 767; Heathcock, C.H. in Asymmetric Synthesis, Morrison, J.D., Ed. Academic, Orlando, Fla., 1984; Evans, D.A. Aldrichimica Acta 1982, 15, 23; Masamune, S.; Choy, W. Aldrichimica Acta 1982, 15, 47; Still, W.C.; Barrish, J.C. J. Am. Chem. Soc. 1983, 105, 2487; Mukaiyama, T. Org. React. 1982, 28, 103.
15. 5. For representative methdology and a historical perspective, see Roush, W.R.; Palkowitz, A.D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348; Hanessian, S. Aldrichimica Acta 1989, 22, 3; Stork, G.; Rychnovsky, S. Pure Appl. Chem. 1986, 55, 767; Heathcock, C.H. in Asymmetric Synthesis, Morrison, J.D., Ed. Academic, Orlando, Fla., 1984; Evans, D.A. Aldrichimica Acta 1982, 15, 23; Masamune, S.; Choy, W. Aldrichimica Acta 1982, 15, 47; Still, W.C.; Barrish, J.C. J. Am. Chem. Soc. 1983, 105, 2487; Mukaiyama, T. Org. React. 1982, 28, 103.
16. 5. For representative methdology and a historical perspective, see Roush, W.R.; Palkowitz, A.D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348; Hanessian, S. Aldrichimica Acta 1989, 22, 3; Stork, G.; Rychnovsky, S. Pure Appl. Chem. 1986, 55, 767; Heathcock, C.H. in Asymmetric Synthesis, Morrison, J.D., Ed. Academic, Orlando, Fla., 1984; Evans, D.A. Aldrichimica Acta 1982, 15, 23; Masamune, S.; Choy, W. Aldrichimica Acta 1982, 15, 47; Still, W.C.; Barrish, J.C. J. Am. Chem. Soc. 1983, 105, 2487; Mukaiyama, T. Org. React. 1982, 28, 103.
17. 5. For representative methdology and a historical perspective, see Roush, W.R.; Palkowitz, A.D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348; Hanessian, S. Aldrichimica Acta 1989, 22, 3; Stork, G.; Rychnovsky, S. Pure Appl. Chem. 1986, 55, 767; Heathcock, C.H. in Asymmetric Synthesis, Morrison, J.D., Ed. Academic, Orlando, Fla., 1984; Evans, D.A. Aldrichimica Acta 1982, 15, 23; Masamune, S.; Choy, W. Aldrichimica Acta 1982, 15, 47; Still, W.C.; Barrish, J.C. J. Am. Chem. Soc. 1983, 105, 2487; Mukaiyama, T. Org. React. 1982, 28, 103.
18. 5. For representative methdology and a historical perspective, see Roush, W.R.; Palkowitz, A.D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348; Hanessian, S. Aldrichimica Acta 1989, 22, 3; Stork, G.; Rychnovsky, S. Pure Appl. Chem. 1986, 55, 767; Heathcock, C.H. in Asymmetric Synthesis, Morrison, J.D., Ed. Academic, Orlando, Fla., 1984; Evans, D.A. Aldrichimica Acta 1982, 15, 23; Masamune, S.; Choy, W. Aldrichimica Acta 1982, 15, 47; Still, W.C.; Barrish, J.C. J. Am. Chem. Soc. 1983, 105, 2487; Mukaiyama, T. Org. React. 1982, 28, 103.
19. 5. For representative methdology and a historical perspective, see Roush, W.R.; Palkowitz, A.D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348; Hanessian, S. Aldrichimica Acta 1989, 22, 3; Stork, G.; Rychnovsky, S. Pure Appl. Chem. 1986, 55, 767; Heathcock, C.H. in Asymmetric Synthesis, Morrison, J.D., Ed. Academic, Orlando, Fla., 1984; Evans, D.A. Aldrichimica Acta 1982, 15, 23; Masamune, S.; Choy, W. Aldrichimica Acta 1982, 15, 47; Still, W.C.; Barrish, J.C. J. Am. Chem. Soc. 1983, 105, 2487; Mukaiyama, T. Org. React. 1982, 28, 103.
20. 6. Hanessian, S.; Sumi, K. Synthesis 1991, 1083.
21. 7. Gung, B.W.; Francis, M.B. J. Org. Chem. 1993, 58, 6177; Dorigo, A.E.; Morokuma, K. J. Am. Chem. Soc. 1989, 111, 6524.
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23. 8. For other selected examples, see Yamamoto, Y.; Chounan, Y.; Nishi, S.; Ibuka, T., Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652; Nemoto, H.; Ando, M.; Fukumoto, K. Tetrahedron Lett. 1990, 31, 6205; Larcheveque, M.; Tamagan, G. Petit, Y. J. Chem. Soc., Chem. Comm. 1989, 31; Roush, W.R.; Lesur, B.M. Tetrahedron Lett. 1983, 24, 2231; Ziegler, F.E.; Gilligan, P.J. J. Org. Chem. 1981, 46, 3874.
24. 8. For other selected examples, see Yamamoto, Y.; Chounan, Y.; Nishi, S.; Ibuka, T., Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652; Nemoto, H.; Ando, M.; Fukumoto, K. Tetrahedron Lett. 1990, 31, 6205; Larcheveque, M.; Tamagan, G. Petit, Y. J. Chem. Soc., Chem. Comm. 1989, 31; Roush, W.R.; Lesur, B.M. Tetrahedron Lett. 1983, 24, 2231; Ziegler, F.E.; Gilligan, P.J. J. Org. Chem. 1981, 46, 3874.
25. 8. For other selected examples, see Yamamoto, Y.; Chounan, Y.; Nishi, S.; Ibuka, T., Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652; Nemoto, H.; Ando, M.; Fukumoto, K. Tetrahedron Lett. 1990, 31, 6205; Larcheveque, M.; Tamagan, G. Petit, Y. J. Chem. Soc., Chem. Comm. 1989, 31; Roush, W.R.; Lesur, B.M. Tetrahedron Lett. 1983, 24, 2231; Ziegler, F.E.; Gilligan, P.J. J. Org. Chem. 1981, 46, 3874.
26. 8. For other selected examples, see Yamamoto, Y.; Chounan, Y.; Nishi, S.; Ibuka, T., Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652; Nemoto, H.; Ando, M.; Fukumoto, K. Tetrahedron Lett. 1990, 31, 6205; Larcheveque, M.; Tamagan, G. Petit, Y. J. Chem. Soc., Chem. Comm. 1989, 31; Roush, W.R.; Lesur, B.M. Tetrahedron Lett. 1983, 24, 2231; Ziegler, F.E.; Gilligan, P.J. J. Org. Chem. 1981, 46, 3874.
27. 8. For other selected examples, see Yamamoto, Y.; Chounan, Y.; Nishi, S.; Ibuka, T., Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652; Nemoto, H.; Ando, M.; Fukumoto, K. Tetrahedron Lett. 1990, 31, 6205; Larcheveque, M.; Tamagan, G. Petit, Y. J. Chem. Soc., Chem. Comm. 1989, 31; Roush, W.R.; Lesur, B.M. Tetrahedron Lett. 1983, 24, 2231; Nicolaou, K.C.; Pavia, M.R.; Seitz, S.P. J. Am. Chem. Soc. 1981, 103, 1224; Ziegler, F.E.; Gilligan, P.J. J. Org. Chem. 1981, 46, 3874.
28. 8. For other selected examples, see Yamamoto, Y.; Chounan, Y.; Nishi, S.; Ibuka, T., Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652; Nemoto, H.; Ando, M.; Fukumoto, K. Tetrahedron Lett. 1990, 31, 6205; Larcheveque, M.; Tamagan, G. Petit, Y. J. Chem. Soc., Chem. Comm. 1989, 31; Roush, W.R.; Lesur, B.M. Tetrahedron Lett. 1983, 24, 2231; Ziegler, F.E.; Gilligan, P.J. J. Org. Chem. 1981, 46, 3874.
29. 9. For conjugate additions to α,β-unsaturated esters, see Lipshutz, B.H.; Ellsworth, E.L.; Dimock, S.H. J. Am. Chem. Soc. 1990, 112, 5869; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947; Eis, M.J.; Wrobel, J.E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693; For a recent monograph, see Perlmutter, P. Conjugate Addition Reaction in Organic Synthesis, Pergamon, New York, N.Y. 1992.
30. 9. For conjugate additions to α,β-unsaturated esters, see Lipshutz, B.H.; Ellsworth, E.L.; Dimock, S.H. J. Am. Chem. Soc. 1990, 112, 5869; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947; Eis, M.J.; Wrobel, J.E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693; For a recent monograph, see Perlmutter, P. Conjugate Addition Reaction in Organic Synthesis, Pergamon, New York, N.Y. 1992.
31. 9. For conjugate additions to α,β-unsaturated esters, see Lipshutz, B.H.; Ellsworth, E.L.; Dimock, S.H. J. Am. Chem. Soc. 1990, 112, 5869; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947; Eis, M.J.; Wrobel, J.E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693; For a recent monograph, see Perlmutter, P. Conjugate Addition Reaction in Organic Synthesis, Pergamon, New York, N.Y. 1992.
32. 9. For conjugate additions to α,β-unsaturated esters, see Lipshutz, B.H.; Ellsworth, E.L.; Dimock, S.H. J. Am. Chem. Soc. 1990, 112, 5869; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947; Eis, M.J.; Wrobel, J.E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693; For a recent monograph, see Perlmutter, P. Conjugate Addition Reaction in Organic Synthesis, Pergamon, New York, N.Y. 1992.
33. 10. Hanessian, S.; Murray, P.J. Tetrahedron 1987, 43, 5055; Hanessian, S.; Murray, P.J.; Sahoo, S. Tetrahedron Lett. 1985, 26, 5627.
34. 10. Hanessian, S.; Murray, P.J. Tetrahedron 1987, 43, 5055; Hanessian, S.; Murray, P.J.; Sahoo, S. Tetrahedron Lett. 1985, 26, 5627.
35. 11. Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 16971.
36. 12. Hanessian, S.; Murray, P.J. J. Org. Chem. 1987, 52, 1170.
37. 13. For some alternative methods, see Ireland, R.E.; Varney, M.D. J. Am. Chem. Soc. 1984, 106, 3668; Oppolzer, W.; Kingma, A.J.; Poli, G. Tetrahedron 1989, 45, 479.
38. 13. For some alternative methods, see Ireland, R.E.; Varney, M.D. J. Am. Chem. Soc. 1984, 106, 3668; Oppolzer, W.; Kingma, A.J.; Poli, G. Tetrahedron 1989, 45, 479.
39. 14. Vishwarkarma, L.C.; Slunger, O.D.; Davis, F.A. Org. Syn. 1986, 66, 203.
40. 15. Morizawa, Y.; Yasuda, A.; Uchida, Tetrahedron Lett. 1986, 27, 1833; See also, Padden-Row, M.N.; Rondan, N.G.; Houk, K.N. J. Am. Chem. Soc. 1982, 104, 7162; Fleming, I.; Lewis, J.J. JCS Chem. Comm. 1985, 149.
41. 15. Morizawa, Y.; Yasuda, A.; Uchida, Tetrahedron Lett. 1986, 27, 1833; See also, Padden-Row, M.N.; Rondan, N.G.; Houk, K.N. J. Am. Chem. Soc. 1982, 104, 7162; Fleming, I.; Lewis, J.J. JCS Chem. Comm. 1985, 149.
42. 15. Morizawa, Y.; Yasuda, A.; Uchida, Tetrahedron Lett. 1986, 27, 1833; See also, Padden-Row, M.N.; Rondan, N.G.; Houk, K.N. J. Am. Chem. Soc. 1982, 104, 7162; Fleming, I.; Lewis, J.J. JCS Chem. Comm. 1985, 149.
43. 16. Vedejs, E.; Larsen, S. J. Org. Chem. 1985, 64, 127.
44. 17. For a recent example of an alternative approach see, Szymoniak, J.; Lefranc, H.; Moïse, C. J. Org. Chem. 1996, 61, 3926 and references cited therein.