Regioselective allylzincation of alkenylboronate

Organic Letters

Volumn 3, Issue 20, 2001, Pages 3137-3140

  Nakamura, Masaharu ^a   Hara, Kenji ^a   Hatakeyama, Takuji ^b   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000814947     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0164637     Document Type: Article

References (30)

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2. (a) Nakamura, M.; Hara, K.; Sakata, G.; Nakamura, E. Org. Lett. 1999, 1, 1505-1507.
3. (b) Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett. 1998, 39, 2157-2158.
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8. For representative examples, see: (a) Itami, K.; Mitsudo, K.; Yoshida, J.-i. Angew. Chem., Int. Ed. 2001, 40, 2337-2339.
9. (b) Nakamura, M.; Inoue, T.; Sato, A.; Nakamura, E. Org. Lett. 2000, 2, 2193-2196.
10. Tamao, K.; Kanatani, R.; Kumada, M. Tetrahedron Lett. 1984, 25, 1913-1916.
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13. There is only one report on the carbometalation of alkenylborane, in which the carbolithiation reaction of 1-(dimesityl)boryl-1-silylalkenes was examined: Cooke, M. P., Jr.; Widener, R. K. J. Am. Chem. Soc. 1987, 709, 931-933. Boryl substitution activates the carbon-carbon triple bond as well as the olefinic double bond toward intramolecular carbolithiation reaction: Cooke, M. P., Jr. J. Org. Chem. 1994, 59, 2930-2931.
14. There is only one report on the carbometalation of alkenylborane, in which the carbolithiation reaction of 1-(dimesityl)boryl-1-silylalkenes was examined: Cooke, M. P., Jr.; Widener, R. K. J. Am. Chem. Soc. 1987, 709, 931-933. Boryl substitution activates the carbon-carbon triple bond as well as the olefinic double bond toward intramolecular carbolithiation reaction: Cooke, M. P., Jr. J. Org. Chem. 1994, 59, 2930-2931.
15. Knochel, P. J. Am. Chem. Soc. 1990, 112, 7431-7433.
16. For reviews see: Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds; Academic Press: New York, 1998. Vaultier, M.; Carboni, B. In Comprehensive Organometallic Chemistry II; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds; Pergammon: Oxford, 1995; Vol. 11, pp 191-276.
17. For reviews see: Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds; Academic Press: New York, 1998. Vaultier, M.; Carboni, B. In Comprehensive Organometallic Chemistry II; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds; Pergammon: Oxford, 1995; Vol. 11, pp 191-276.
18. (a) Hirai, A.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 11791-11798.
19. (b) Hirai, A.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1999, 121, 8665-8666. See also:
20. Marek, I.; Schreiner, P. R.; Normant, J. F. Org. Lett. 1999, 1, 929-931.
21. (a) Gaudemar, M. C. R. Séances Acad. Sci., Sér. C 1971, 273, 1669-1672.
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23. The reaction with allylmagnesium bromide and allyllithium resulted largely in the loss of the material with some recovery of the vinylboronate (8% and 30%, respectively).
24. f= 0.24, 5% EtOAc in hexane). Further purification was, if necessary, carried out by silica gel chromatography.
25. Compare: Kubota, K.; Mori, S.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1998, 120, 13334-13341.
26. In the reaction of 1-boryl-1-propene, the regioselectivity as to the allylic zinc reagent eroded and gave a nearly 1:1 mixture of α-and γ-regioisomers. The diastereoselectivity as to the newly formed C-C bond was also very low.
27. The oxidation was performed according to Knochel's procedure with slight modification: Knochel, P. Tetrahedron Lett. 1988, 29, 6697-6700. See also ref 2a.
28. 15 Geometry optimization was performed with the hybrid B3LYP density functional by using Ahlrichs' SVP basis set for Zn and 6-31+G(d) basis set for the rest (denoted as B3LYP/631A). The basis sets are implemented in the program.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J., Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
30. Theoretical details including discussion on the electronic properties of the transition structures will be reported in a full paper.