Enhanced diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes obtained from nerol and geraniol

Tetrahedron

Volumn 52, Issue 27, 1996, Pages 9047-9056

  Nacro, Kassoum ^a   Baltas, Michel ^a   Escudier, Jean Marc ^a   Gorrichon, Liliane ^a  

^a UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

diastereoselection; enolate; optically active , epoxy hydroxyesters

Indexed keywords

GERANIOL; NEROL; TERPENE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030185484     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00453-X     Document Type: Article

References (27)

1. 1 Corey, E.J.; Cheng, X.M., The logic of chemical synthesis; Wiley: New York, 1983.
2. 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
3. 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
4. 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
5. 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
6. 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
7. 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
8. 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
9. 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
10. 2 For some publications and references cited therein: Henderson, I.; Sharpless, K.B.; Wong, C.H. J. Am. Chem. Soc. 1994, 116, 558-561. Lin, C.H.; Sugai, T.; Halcomb, R.L.; Ichikawa, Y.; Wong, C.H. J. Am. Chem. Soc. 1992, 114, 10138-10145. Evans, D.A.; Gauchet-Prunet, J.A.; Carreira, E.M.; Charette, A.B. J. Org. Chem. 1991, 56, 741-750. Dondoni, A.J.; Merino, P. Synthesis 1992, 196-200. Roush, W.R.; Straub, J.A.; Vannieuwenhze, M.S. J. Org. Chem. 1991, 56, 1636-1648. Danishefski, S.J. Aldrichim. Acta 1986, 19, 59-69. Braun, M. Angew.Chem.Int.Ed. 1987, 26, 24-37. Nicolaou, K.C. Aldrichim. Acta 1993, 26, 63-77. Danishefsky, S.J.; DeNinno, M.P.; Chen, S.H. J. Am. Chem. Soc. 1988, 110, 3929-3940.
11. 3 Escudier, J.M., Baltas, M.; Gorrichon, L. Tetrahedron 1993, 49, 5253-5266.
12. 4 Escudier, J.M., Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1992, 33, 1439-1442.
13. 5 a) Sharpless, K.B.; Umbreit, M.A. J. Am. Chem. Soc. 1977, 99, 5526-5528.
14. b) Paterson, I.; Boddy, I.; Mason, I. Tetrahedron Lett. 1987, 28, 5205-5208, Paterson, I.; Tillyer, R.D.; Smaill J.B. Tetrahedron Lett. 1993, 34, 7137-7140 and references cited therein.
15. b) Paterson, I.; Boddy, I.; Mason, I. Tetrahedron Lett. 1987, 28, 5205-5208, Paterson, I.; Tillyer, R.D.; Smaill J.B. Tetrahedron Lett. 1993, 34, 7137-7140 and references cited therein.
16. 6 Gao, Y.; Hanson, R.M.; Klunder, J.M.; Ko, S.Y.; Masamune, H.; Sharpless, K.B. J. Am. Chem. Soc. 1987, 109, 5765-5780. Katsuki, T.; Sharpless, K.B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
17. 6 Gao, Y.; Hanson, R.M.; Klunder, J.M.; Ko, S.Y.; Masamune, H.; Sharpless, K.B. J. Am. Chem. Soc. 1987, 109, 5765-5780. Katsuki, T.; Sharpless, K.B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
18. 7 Mori, N.; Kuwahara, Y. Tetrahedron Lett. 1995, 36, 1477-1478.
19. 8 Parikh, J.R.; Von Doering, E.W. J. Am. Chem. Soc. 1967, 89, 5505-5507.
20. 9 Nicolaou, K.C.; Daines, R.A.; Uenishi, J.; Li, W.S.; Papahatjis, D.P.; Chakraborty, T.K. J. Am. Chem. Soc. 1988, 110, 4672-4685.
21. 10 Rychnovsky, S.D.; Rogers, B.; Young, G. J. Org. Chem. 1993, 58, 3511-3515.
22. 11 Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204 and 2205-2208. Anh, N.T.; Eisenstein, O. Nouv. J. chim. 1977, 1, 61-70. Cornforth, J.W.; Cornforth, R.H.; Methew, K.K. J. Chem. Soc. 1959, 112-116.
23. 11 Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204 and 2205-2208. Anh, N.T.; Eisenstein, O. Nouv. J. chim. 1977, 1, 61-70. Cornforth, J.W.; Cornforth, R.H.; Methew, K.K. J. Chem. Soc. 1959, 112-116.
24. 11 Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204 and 2205-2208. Anh, N.T.; Eisenstein, O. Nouv. J. chim. 1977, 1, 61-70. Cornforth, J.W.; Cornforth, R.H.; Methew, K.K. J. Chem. Soc. 1959, 112-116.
25. 12 Frenking, G.; Köhler, K.F.; Reetz, M.T. Tetrahedron 1991, 47, 8991-9004, 9005-9018 and references cited therein.
26. 13 Molecular mechanic calculations were obtained from a PC-Model (4.0 version) and a MMX force field Programme of Allinger N.L. modified by Gajiewski J.J. and Gilbert F.E. (Serena Software, Bloomington, USA).
27. 2Oep:-63° ∼conf. III