Chirality transfer via the palladium-catalyzed cross-coupling reaction of optically active 2-cyclohexenylsilane: Stereochemical and mechanistic aspects

Organometallics

Volumn 15, Issue 26, 1996, Pages 5762-5765

  Hiyama, Tamejiro ^a   Matsuhashi, Hayao ^a   Fujita, Akinori ^a   Tanaka, Makoto ^a   Hirabayashi, Kazunori ^a   Shimizu, Masaki ^a   Mori, Atsunori ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000511533     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960750a     Document Type: Article

References (21)

1. Reviews on cross-coupling reactions of several metals: Kumada, M. Pure Appl. Chem. 1980, 52, 669. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Negishi, E. Acc. Chem. Res. 1982, 15, 340. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Posner, G. H. Org. React. 1975, 22, 253.
2. Reviews on cross-coupling reactions of several metals: Kumada, M. Pure Appl. Chem. 1980, 52, 669. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Negishi, E. Acc. Chem. Res. 1982, 15, 340. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Posner, G. H. Org. React. 1975, 22, 253.
3. Reviews on cross-coupling reactions of several metals: Kumada, M. Pure Appl. Chem. 1980, 52, 669. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Negishi, E. Acc. Chem. Res. 1982, 15, 340. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Posner, G. H. Org. React. 1975, 22, 253.
4. Reviews on cross-coupling reactions of several metals: Kumada, M. Pure Appl. Chem. 1980, 52, 669. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Negishi, E. Acc. Chem. Res. 1982, 15, 340. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Posner, G. H. Org. React. 1975, 22, 253.
5. Reviews on cross-coupling reactions of several metals: Kumada, M. Pure Appl. Chem. 1980, 52, 669. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Negishi, E. Acc. Chem. Res. 1982, 15, 340. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Posner, G. H. Org. React. 1975, 22, 253.
6. Hatanaka, Y.; Hiyama, T. Synlett 1991, 845. Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471.
7. Hatanaka, Y.; Hiyama, T. Synlett 1991, 845. Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471.
8. (a) Ohmura, H.; Matsuhashi, H.; Tanaka, M.; Kuroboshi, M.; Hiyama, T. J. Organomet. Chem. 1995, 499, 167.
9. See also: (b) Hayashi, T.; Kabeta, K.; Yamamoto, T.; Tamao, K.; Kumada, M. Tetrahedron Lett. 1983, 24, 5661. (c) Kitayama, K.; Tsuji, H.; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1996, 37, 4169.
10. See also: (b) Hayashi, T.; Kabeta, K.; Yamamoto, T.; Tamao, K.; Kumada, M. Tetrahedron Lett. 1983, 24, 5661. (c) Kitayama, K.; Tsuji, H.; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1996, 37, 4169.
11. The stereochemical dependence on fluoride reagent was again observed in the reaction of 1 with aldehyde. The reaction of (S)-1 with benzaldehyde in the presence of (TAS)F afforded the corresponding product with high degrees of chirality transfer (>95%) as well as high diastereoselectivity. However, the use of CsF as the activator considerably decreased the stereoselectivity. Hirabayashi, K.; Matsuhashi, H.; Mori, A.; Hiyama, T. Unpublished results. (Formula Presented) syn anti TASF: syn: anti = 23: 1 CsF: syn: anti = 2: 1 See also: Kira, M.; Hino, T.; Sakurai, H. Tetrahedron Lett. 1989, 30, 1099. Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
12. The stereochemical dependence on fluoride reagent was again observed in the reaction of 1 with aldehyde. The reaction of (S)-1 with benzaldehyde in the presence of (TAS)F afforded the corresponding product with high degrees of chirality transfer (>95%) as well as high diastereoselectivity. However, the use of CsF as the activator considerably decreased the stereoselectivity. Hirabayashi, K.; Matsuhashi, H.; Mori, A.; Hiyama, T. Unpublished results. (Formula Presented) syn anti TASF: syn: anti = 23: 1 CsF: syn: anti = 2: 1 See also: Kira, M.; Hino, T.; Sakurai, H. Tetrahedron Lett. 1989, 30, 1099. Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
13. The stereochemical dependence on fluoride reagent was again observed in the reaction of 1 with aldehyde. The reaction of (S)-1 with benzaldehyde in the presence of (TAS)F afforded the corresponding product with high degrees of chirality transfer (>95%) as well as high diastereoselectivity. However, the use of CsF as the activator considerably decreased the stereoselectivity. Hirabayashi, K.; Matsuhashi, H.; Mori, A.; Hiyama, T. Unpublished results. (Formula Presented) syn anti TASF: syn: anti = 23: 1 CsF: syn: anti = 2: 1 See also: Kira, M.; Hino, T.; Sakurai, H. Tetrahedron Lett. 1989, 30, 1099. Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
14. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
15. The authors are grateful to Dr. K. Kitayam for fruitful suggestions. See also ref 3c.
16. 1H COSY spectrum exhibits strong correlation between protons at C(3) and C(4) suggesting that both protons are axial.
17. 2H NMR spectrum analysis. Thus, scrambling of the stereochemistry is ascribed to the low facial selectivity at γ-position.
18. Hatanaka, Y.; Goda, K.-i.; Hiyama, T. Tetrahedron Lett. 1994, 35, 1279. See also: Hatanaka, Y.; Ebina, Y.; Hiyama, T. J. Am. Chem. Soc. 1991, 113, 7075.
19. Hatanaka, Y.; Goda, K.-i.; Hiyama, T. Tetrahedron Lett. 1994, 35, 1279. See also: Hatanaka, Y.; Ebina, Y.; Hiyama, T. J. Am. Chem. Soc. 1991, 113, 7075.
20. Hatanaka, Y.; Goda, K.-i.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6511.
21. R = 9.12 min (minor enantiomer) and 11.35 min (major enantiomer) for 58% ee of the (S)-isomer) of the optically active (3-cyclohexenyl)benzene. Cf.: Consiglio, G.; Piccolo, O.; Roncetti, L.; Morandini, F. Tetrahedron 1986, 42, 2043.