Allylmanganation and diallylation of acetylenic compounds

Tetrahedron

Volumn 53, Issue 14, 1997, Pages 5061-5072

  Tang, Jun ^a   Okada, Kenji ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; MANGANESE DERIVATIVE;

ARTICLE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030948076     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00201-9     Document Type: Article

References (38)

1. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 and references cited therein. Recently a conjugate addition of the allylic copper species has been reported. Lipshutz, B. H.; Hackmann, C. J. Org. Chem. 1994, 59, 7437.
2. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 and references cited therein. Recently a conjugate addition of the allylic copper species has been reported. Lipshutz, B. H.; Hackmann, C. J. Org. Chem. 1994, 59, 7437.
3. Knochel, P. "Carbometallation of Alkenes and Alkynes" in Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, Vol. 4, p. 865; Oppolzer, W. "Metallo-ene Reactions" in Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, Vol. 5, p. 29.
4. Knochel, P. "Carbometallation of Alkenes and Alkynes" in Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, Vol. 4, p. 865; Oppolzer, W. "Metallo-ene Reactions" in Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, Vol. 5, p. 29.
5. Normant, J. F.; Alexakis, A. Synthesis 1981, 841; von Rein, F. W.; Richey, Jr. H. G.; Tetrahedron Lett. 1971, 3777.
6. Normant, J. F.; Alexakis, A. Synthesis 1981, 841; von Rein, F. W.; Richey, Jr. H. G.; Tetrahedron Lett. 1971, 3777.
7. Jousseaume, B.; Duboudin, J.-G. J. Organomet. Chem. 1975, 91, Cl. Conjugate addition of the allylic copper species has been reported: Lipshutz, B. H.; Hackmann, C. J. Org. Chem. 1994, 59, 7437.
8. Jousseaume, B.; Duboudin, J.-G. J. Organomet. Chem. 1975, 91, Cl. Conjugate addition of the allylic copper species has been reported: Lipshutz, B. H.; Hackmann, C. J. Org. Chem. 1994, 59, 7437.
9. Bernadou, F.; Miginiac, L. Tetrahedron Lett. 1976, 3083; Mauze, B.; Nivert, C.; Miginiac, L. J. Organomet. Chem. 1972, 44, 69; Bellassoued, M.; Frangin, Y. Synthesis. 1978, 838.
10. Bernadou, F.; Miginiac, L. Tetrahedron Lett. 1976, 3083; Mauze, B.; Nivert, C.; Miginiac, L. J. Organomet. Chem. 1972, 44, 69; Bellassoued, M.; Frangin, Y. Synthesis. 1978, 838.
11. Bernadou, F.; Miginiac, L. Tetrahedron Lett. 1976, 3083; Mauze, B.; Nivert, C.; Miginiac, L. J. Organomet. Chem. 1972, 44, 69; Bellassoued, M.; Frangin, Y. Synthesis. 1978, 838.
12. Further examples of the addition of other allylic organometallic reagents to alkynes are as follows. Allylic aluminum reagents; Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. Negishi, E.; Takahashi, T. Synthesis 1988, 1. Allylic indium reagents: Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581. Allylic boron reagents: Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505; idem. Organomet. Chem. Rev. 1972, 8[A], 1.
13. Further examples of the addition of other allylic organometallic reagents to alkynes are as follows. Allylic aluminum reagents; Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. Negishi, E.; Takahashi, T. Synthesis 1988, 1. Allylic indium reagents: Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581. Allylic boron reagents: Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505; idem. Organomet. Chem. Rev. 1972, 8[A], 1.
14. Further examples of the addition of other allylic organometallic reagents to alkynes are as follows. Allylic aluminum reagents; Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. Negishi, E.; Takahashi, T. Synthesis 1988, 1. Allylic indium reagents: Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581. Allylic boron reagents: Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505; idem. Organomet. Chem. Rev. 1972, 8[A], 1.
15. Further examples of the addition of other allylic organometallic reagents to alkynes are as follows. Allylic aluminum reagents; Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. Negishi, E.; Takahashi, T. Synthesis 1988, 1. Allylic indium reagents: Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581. Allylic boron reagents: Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505; idem. Organomet. Chem. Rev. 1972, 8[A], 1.
16. Further examples of the addition of other allylic organometallic reagents to alkynes are as follows. Allylic aluminum reagents; Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. Negishi, E.; Takahashi, T. Synthesis 1988, 1. Allylic indium reagents: Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581. Allylic boron reagents: Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505; idem. Organomet. Chem. Rev. 1972, 8[A], 1.
17. A part of this work was published in a communication. Okada, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc., 1996, 118, 6076.
18. a) Hibino, J.; Nakatsukasa, S.; Fugami, K.; Matsubara, S.; Oshima, K..; Nozaki, H. J. Am. Chem. Soc., 1985, 107, 6416.
19. b) Fugami, K.; Nakatsukasa, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Chem. Lett., 1986, 869.
20. c) Fugami, K.; Hibino, J.; Nakatsukasa, S.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron, 1988, 44, 4277.
21. An allylic manganese reagent denved from allylic bromide and Mn(0) has been reported to react with aldehydes, providing homoallylic alcohols. Hiyama, T.; Obayashi, M.; Nakamura, A.; Organometallics 1982, 1, 1249. Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37, 7049; Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009.
22. An allylic manganese reagent denved from allylic bromide and Mn(0) has been reported to react with aldehydes, providing homoallylic alcohols. Hiyama, T.; Obayashi, M.; Nakamura, A.; Organometallics 1982, 1, 1249. Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37, 7049; Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009.
23. An allylic manganese reagent denved from allylic bromide and Mn(0) has been reported to react with aldehydes, providing homoallylic alcohols. Hiyama, T.; Obayashi, M.; Nakamura, A.; Organometallics 1982, 1, 1249. Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37, 7049; Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009.
24. 4] have been reported. Morris, R. J.; Girolami, G. S. Organometallics 1989, 8, 1478-1485. Cahiez et al. have reported the reaction of tetrafurylmanganate. Cahiez, G.; Chavant, P.-Y.; Metais, E. Tetrahedron Lett. 1992, 33, 5245.
25. 4] have been reported. Morris, R. J.; Girolami, G. S. Organometallics 1989, 8, 1478-1485. Cahiez et al. have reported the reaction of tetrafurylmanganate. Cahiez, G.; Chavant, P.-Y.; Metais, E. Tetrahedron Lett. 1992, 33, 5245.
26. 4] have been reported. Morris, R. J.; Girolami, G. S. Organometallics 1989, 8, 1478-1485. Cahiez et al. have reported the reaction of tetrafurylmanganate. Cahiez, G.; Chavant, P.-Y.; Metais, E. Tetrahedron Lett. 1992, 33, 5245.
27. In the absence of HMPA, displacement of the metaloxy (OMtI) group by the allylic anion proceeded to give an allenyl compound as by-product. The addition of HMPA could suppress the formation of the allenic product.
28. 10 the reaction of propargylic alcohols was performed with trialIylmanganate.
29. 2 catalyst gave allylated product in 48% yield along with recovered starting alcohol 7a (36%).
30. 2, ether was used because of its solubility.
31. 2 (3 mol%) in ether at 25°C for 3 h. After heating at reflex for 10 h, 4a was obtained in 48% yield, but Sa was obtained in only <5% yield.
32. Burton, D. J.; Hartgraves, G. A.; Hsu, J. Tetrahedron Lett. 1990, 31, 3699; Westmijze, H.; Vermeer, P. ibid. 1979, 4101; Tadema, G.; Everhardus, R. H.; Westmijze, H.; Vermeer, P. ibid. 1978, 3935;
33. Burton, D. J.; Hartgraves, G. A.; Hsu, J. Tetrahedron Lett. 1990, 31, 3699; Westmijze, H.; Vermeer, P. ibid. 1979, 4101; Tadema, G.; Everhardus, R. H.; Westmijze, H.; Vermeer, P. ibid. 1978, 3935;
34. Burton, D. J.; Hartgraves, G. A.; Hsu, J. Tetrahedron Lett. 1990, 31, 3699; Westmijze, H.; Vermeer, P. ibid. 1979, 4101; Tadema, G.; Everhardus, R. H.; Westmijze, H.; Vermeer, P. ibid. 1978, 3935;
35. Marek, I.; Mangeney, P.; Alexakis, A.; Normant, J. F. ibid. 1986, 27, 5499.
36. 2 provided 15 in only 10% yield along with unidentified complex mixture.
37. The formation of 20b as a mixture of Z/E = 10/90 starting from 16b (Z/E = 90/10) might suggest that both intramolecular carbomanganation and deoxymanganation proceed in syn fashion.
38. We are tempted to assume that reductive elimination from alkenylmanganese intermediate 22 affords the diallylated product in the presence of air. Oxygen would facilitate the reductive elimination but the role of oxygen and precise mechanism of the reaction are not clear at this stage. (Scheme 14). equation presented