Conjugate Allylation to α,β-Unsaturated Aldehydes with the New Chemzyme p-F-ATPH

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 11, 1997, Pages 1183-1185

  Ooi, Takashi ^a   Kondo, Yuichiro ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Allylations; Lewis acids; Michael additions; Regioselectivity

Indexed keywords

EID: 0030790917     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199711831     Document Type: Article

References (27)

1. Reviews: a) E. D. Bergman, D. Ginsburg, R. Pappo, Org. React. 1959, 10, 179; b) H. O. House, Modern Synthetic Reactions, 2nd ed., W. A. Benjamin, Menlo Park, CA, 1972; p 595; c) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
2. Reviews: a) E. D. Bergman, D. Ginsburg, R. Pappo, Org. React. 1959, 10, 179; b) H. O. House, Modern Synthetic Reactions, 2nd ed., W. A. Benjamin, Menlo Park, CA, 1972; p 595; c) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
3. Reviews: a) E. D. Bergman, D. Ginsburg, R. Pappo, Org. React. 1959, 10, 179; b) H. O. House, Modern Synthetic Reactions, 2nd ed., W. A. Benjamin, Menlo Park, CA, 1972; p 595; c) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
4. G. Majetich, A. Casares, D. Chapman, M. Behnke, J. Org. Chem. 1986, 51, 1745.
5. Reviews: a) G. H. Posner, Org. React. 1972, 19, 1; b) Y. Yamamoto, Angew. Chem. 1986, 98, 945; Angew. Chem. Int. Ed. Engl. 1986, 25, 947; c) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135.
6. Reviews: a) G. H. Posner, Org. React. 1972, 19, 1; b) Y. Yamamoto, Angew. Chem. 1986, 98, 945; Angew. Chem. Int. Ed. Engl. 1986, 25, 947; c) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135.
7. Reviews: a) G. H. Posner, Org. React. 1972, 19, 1; b) Y. Yamamoto, Angew. Chem. 1986, 98, 945; Angew. Chem. Int. Ed. Engl. 1986, 25, 947; c) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135.
8. Reviews: a) G. H. Posner, Org. React. 1972, 19, 1; b) Y. Yamamoto, Angew. Chem. 1986, 98, 945; Angew. Chem. Int. Ed. Engl. 1986, 25, 947; c) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135.
9. a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131;
10. b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519;
11. c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091;
12. d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928.
13. a) B. J. Wakefield, The Chemistry of Organolithium Compounds, Pergamon, Oxford, 1974;
14. b) M. A. Beswick, D. S. Wright, Comprehensive Organometallic Chemistry II, Vol. 1 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995 p. 1;
15. c) M. Gray, M. Tinkl, V. Snieckus, Comprehensive Organometallic Chemistry II, Vol. 11 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, p. 1;
16. d) B. J. Wakefield, Organolithium Method, Academic Press, London, 1988.
17. +) coenzyme: F. A. Loewus, F. H. Westheimer, B. Vennesland, J. Am. Chem. Soc. 1953, 75, 5018.
18. 3 in aqueous DME; 3) deprotection of the MOM group with aqueous HCl-dioxane (C. M. Unrau, M. G. Campbell, V. Sniekus, Tetrahedron Lett. 1992, 33, 2773).
19. The influence of para-X substituents (X = Cl, F) on the Lewis acidity of p-X-ATPH seems to be negligible, since the increase of the Lewis acidity of p-X-ATPH would cause the preferential 1,2-addition of BuLi to cinnamaldehyde; see: a) K. N. Houk, R. W. Strozier, J. Am. Chem. Soc. 1973, 95, 4094; b) B. Deschamps, Tetrahedron 1978, 34, 2009.
20. The influence of para-X substituents (X = Cl, F) on the Lewis acidity of p-X-ATPH seems to be negligible, since the increase of the Lewis acidity of p-X-ATPH would cause the preferential 1,2-addition of BuLi to cinnamaldehyde; see: a) K. N. Houk, R. W. Strozier, J. Am. Chem. Soc. 1973, 95, 4094; b) B. Deschamps, Tetrahedron 1978, 34, 2009.
21. For information on the Li-F interaction see: a) N. J. R. van Eikema Hommes, P. von R. Schleyer, Angew. Chem. 1992, 104, 768.; Angew. Chem. Int. Ed. Engl. 1992, 31, 755; b) J. M. Saa, P. M. Deya, G. A. Suner, A. Frontera, J. Am. Chem. Soc. 1992, 114, 9093; c) for details, see: T. Yamazaki, T. Kitazume, J. Synth. Org. Chem. Jpn. 1996, 54, 665.
22. For information on the Li-F interaction see: a) N. J. R. van Eikema Hommes, P. von R. Schleyer, Angew. Chem. 1992, 104, 768.; Angew. Chem. Int. Ed. Engl. 1992, 31, 755; b) J. M. Saa, P. M. Deya, G. A. Suner, A. Frontera, J. Am. Chem. Soc. 1992, 114, 9093; c) for details, see: T. Yamazaki, T. Kitazume, J. Synth. Org. Chem. Jpn. 1996, 54, 665.
23. For information on the Li-F interaction see: a) N. J. R. van Eikema Hommes, P. von R. Schleyer, Angew. Chem. 1992, 104, 768.; Angew. Chem. Int. Ed. Engl. 1992, 31, 755; b) J. M. Saa, P. M. Deya, G. A. Suner, A. Frontera, J. Am. Chem. Soc. 1992, 114, 9093; c) for details, see: T. Yamazaki, T. Kitazume, J. Synth. Org. Chem. Jpn. 1996, 54, 665.
24. For information on the Li-F interaction see: a) N. J. R. van Eikema Hommes, P. von R. Schleyer, Angew. Chem. 1992, 104, 768.; Angew. Chem. Int. Ed. Engl. 1992, 31, 755; b) J. M. Saa, P. M. Deya, G. A. Suner, A. Frontera, J. Am. Chem. Soc. 1992, 114, 9093; c) for details, see: T. Yamazaki, T. Kitazume, J. Synth. Org. Chem. Jpn. 1996, 54, 665.
25. Allyllithium can be generated by treatment of allyltributyltin in THF or DME with BuLi in hexane at -78°C for 30 min [5d]. An ethereal solution of allyllithium was prepared from PhLi in ether and allyltriphenyltin at room temperature: J. J. Eisch, Organomet. Synth. 1981, 2, 92; D. Seyferth, M. A. Weiner, Org. Synth. Collect. Vol. V, 1973, 452.
26. Allyllithium can be generated by treatment of allyltributyltin in THF or DME with BuLi in hexane at -78°C for 30 min [5d]. An ethereal solution of allyllithium was prepared from PhLi in ether and allyltriphenyltin at room temperature: J. J. Eisch, Organomet. Synth. 1981, 2, 92; D. Seyferth, M. A. Weiner, Org. Synth. Collect. Vol. V, 1973, 452.
27. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207.