The olefinic aldol reaction. Addition of zincated hydrazone to vinylsilane

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 7099-7102

  Nakamura, Eiichi ^a   Kubota, Katsumi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZONE DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030819610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01712-7     Document Type: Article

References (22)

1. (a) Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792-793;
2. (b) Kubota, K.; Nakamura, E. Angew. Chem., in press.
3. Karoyan, P.; Chassaing, G. Tetrahedron Lett. 1997, 38, 85-88; Lorthiois, E.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1997, 38, 89-92.
4. Karoyan, P.; Chassaing, G. Tetrahedron Lett. 1997, 38, 85-88; Lorthiois, E.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1997, 38, 89-92.
5. Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5867-5868. Nakamura, E. Pure Appl. Chem. 1996, 68, 123-130. Nakamura, E. J. Synth. Org. Chem. Jpn. 1994, 51, 985-994.
6. Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5867-5868. Nakamura, E. Pure Appl. Chem. 1996, 68, 123-130. Nakamura, E. J. Synth. Org. Chem. Jpn. 1994, 51, 985-994.
7. Kubota, K.; Nakamura, M.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5867-5868. Nakamura, E. Pure Appl. Chem. 1996, 68, 123-130. Nakamura, E. J. Synth. Org. Chem. Jpn. 1994, 51, 985-994.
8. While the intramolecular reaction in ref 2 took place with a BuZn(II) cation, we found that the BuZn(II) cation also serves well for intramolecular reactions (to be published).
9. Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458.
10. Thus, the reaction of ethylene with zincated hydrazone at room temperature takes 4 days for completion, and that of styrene is halfway to completion even after 1 week.
11. For the ability of vinylsilane to accept nucleophiles, see: Seyferth, D.; Wada, T. Inorg. Chem. 1962, 1, 78-83. Stober, M.; Michael, K. W.; Speier, J. L. J. Org. Chem. 1967, 32, 2740-2744. Tamao, K.; Kanatani, R.; Kumada, M. Tetrahedron Lett. 1984, 25, 1913-1916.
12. For the ability of vinylsilane to accept nucleophiles, see: Seyferth, D.; Wada, T. Inorg. Chem. 1962, 1, 78-83. Stober, M.; Michael, K. W.; Speier, J. L. J. Org. Chem. 1967, 32, 2740-2744. Tamao, K.; Kanatani, R.; Kumada, M. Tetrahedron Lett. 1984, 25, 1913-1916.
13. For the ability of vinylsilane to accept nucleophiles, see: Seyferth, D.; Wada, T. Inorg. Chem. 1962, 1, 78-83. Stober, M.; Michael, K. W.; Speier, J. L. J. Org. Chem. 1967, 32, 2740-2744. Tamao, K.; Kanatani, R.; Kumada, M. Tetrahedron Lett. 1984, 25, 1913-1916.
14. For utility of hydrazones, see: Bergbreiter, D. E.; Momongan, M. in Comprehensive Organic Synthesis; B. M. Trost and I. Fleming, Eds.; Pergamon press: Oxford, 1991; Vol. 2, pp. 503-526.
15. 2O in hexane) afforded 2.66 g of 1-iodo-3-methyl-1-trimethylsilyl-4-hexanone (75% yield) as a 3:2 mixture of diastereomers.
16. Corey, E. J.; Knapp, S. Tetrahedron Lett. 1976, 4687-4690. Hosomi, A.; Araki, Y.; Sakurai, H. J. Am. Chem. Soc. 1982, 104, 2081-2083, and references cited therein.
17. Corey, E. J.; Knapp, S. Tetrahedron Lett. 1976, 4687-4690. Hosomi, A.; Araki, Y.; Sakurai, H. J. Am. Chem. Soc. 1982, 104, 2081-2083, and references cited therein.
18. This is due to regioselective lithiation known for a 2-methylcyclohexanone hydrazone (cf. ref. 8).
19. Electrophilic trapping was successful for the ethylene adducts (ref 1b), wherein the intermediate corresponding to 3 is a primary zinc reagent lacking the silyl group.
20. Nakamura, E.; Miyachi, Y.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 6686-6692. Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Chem. Soc., Faraday Trans. 1994, 29, 1789-1798.
21. Nakamura, E.; Miyachi, Y.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 6686-6692. Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Chem. Soc., Faraday Trans. 1994, 29, 1789-1798.
22. This work was supported by Grant-in-Aid for Scientific Research on Priority Areas (No. 283 , "Innovative Synthetic Reactions") from the Monbusho.