Catalytic Asymmetric Synthesis of Optically Active 2-Alkanols via Hydrosilylation of 1-Alkenes with a Chiral Monophosphine—Palladium Catalyst

Journal of the American Chemical Society

Volumn 113, Issue 26, 1991, Pages 9887-9888

  Uozumi, Yasuhiro ^a   Hayashi, Tamio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85007835900     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00026a044     Document Type: Article

References (34)

1. For recent reviews on catalytic asymmetric reactions: (a) Brunner, H. Synthesis 1988, 645.
2. Brunner, H. Top. Stereochem. 1988, 18, 129.
3. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
4. Noyori, R.; Kitamura, M. Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: New York, 1989; Vol. 5, p 115.
5. Ojima, I.; Clos, N.; Bastos, C. Tetrahedron 1989, 45, 6901.
6. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801 and references cited therein
7. Sharpless, K. B.; Amberg, W.; Beller, M.; Chen, H.; Hartung, J.; Kawanami, Y.; Lübben, D.; Manoury, E.; Ogino, Y.; Shibata, T.; Ukita, T. J. Org. Chem. 1991, 56, 4585 and references cited therein.
8. Asymmetric synthesis of 1-arylethanols via palladium-catalyzed hydrosilylation or rhodium-catalyzed hydroboration of vinylarenes has been reported: (a) Hayashi, T.; Tamao, K.; Katsuro, Y.; Nakae, I.; Kumada, M. Tetrahedron Lett. 1980, 21, 1871.
9. Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426.
10. Zhang, J.; Lou, B.; Guo, G.; Dai, L. J. Org. Chem. 1991, 56, 1670.
11. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694.
12. Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37.
13. Tamao, K.; Nakajo, E.; Ito, Y. J. Org. Chem. 1987, 52, 4412.
14. Tamao, K. In Organosilicon and Bioorganosilicon Chemistry; Sakurai, H., Ed.; Ellis Horwood: Chichester, 1985; p 231.
15. For reviews: (a) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley: Chichester, 1989; p 1479.
16. Speier, J. L. Advanced Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1979; Vol. 17, p 407.
17. Lukevics, E.; Belyakova, Z. V.; Pomerantseva, M. G.; Voronkov, M. G. In Journal of Organometallic Chemistry Library; Seyferth, D., Davies, A. G., Fisher, E. O., Normant, J. F., Reutov, O. A., Eds.; Elsevier: Amsterdam, 1977; Vol. 5.
18. Ojima, I.; Kogure, T. Rev. Silicon, Germanium, Tin Lead Compd. 1981, 5, 1.
19. It has been reported that reaction of 1-octene with HSiCl3 catalyzed by Pd(PPh3)4 at 100 °C gives 1-octylsilane in 85% yield: Tsuji, J.; Hara, M.; Ohno, K. Tetrahedron 1974, 30, 2143.
20. Regioselective hydrosilylation of CF3CH=CH2 with HSiMeCl2 or HSiCl3 catalyzed by PdCl2(PPh3)2 has been reported: Ojima, I.; Yatabe, M.; Fuchikami, T. J. Organomet. Chem. 1984, 260, 335.
21. 1,4-Bis(diphenylphosphino)butane.
22. (S,S)-2,3-Bis(diphenylphosphino)butane: Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262.
23. (R)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl: Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
24. For example, the reaction in the presence of 0.1 mol % of a palladium-triphenylphosphine catalyst (P/Pd = 2/1) at 40 °C for 24 h gave a 12% yield of hexylsilanes consisting of 1- and 2-isomers in a ratio of 91/9, accompanied by isomerization of 1-hexene into internal olefins. See also ref 6.
25. It is reasonable to expect that a monodentate phosphine ligand generates a palladium catalyst that is more active for the hydrosilylation than a chelating bis(phosphine) ligand. The former can form square-planar palladium(II) intermediate PdH(SiCl3)L(CH2=CHR) (L = monophosphine), which offers a coordination site for the activation of olefin.
26. Preparation of (S)-1a from (S)-2′-methoxy-1,1′-binaphthyl-2-carboxylic acid has been reported: Hattori, T.; Shijo, M.; Kumagai, S.; Miyano, S. Chem. Express 1991, 6, 335.
27. The high catalytic activity and regioselectivity of the palladium—MOP complex may be related to the reactivity of key intermediate Pd(2-alkyl)L-(silyl). It seems that MOP ligand can accelerate the reductive elimination of 2-silylalkane and/or retard the β-hydrogen elimination forming 2-alkenes. Triphenylphosphine or tri-o-tolylphosphine caused the isomerization of a terminal olefin into internal olefins during the hydrosilylation while MOP did not (see footnote 11).
28. An example for those reactions is nickel-catalyzed asymmetric cross-coupling: Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153.
29. Kurz, L.; Lee, G.; Morgans, D., Jr.; Waldyke, M. J.; Wars, T. Tetrahedron Lett. 1990, 31, 6321.
30. (S)-la: [α]20D −94.5° (c 0.27, chloroform), [α]16D −59.7° (c 1.40, benzene) (ref 13: [α]% −59.3° (c 1.0, benzene)). (S)-lb: [α]20D −90.0° (c 0.13, chloroform). (S)-lc: [α]20D−96.1° (c 0.12, chloroform). (S)-ld: [α]20D −85.1° (c 0.20, chloroform). Satisfactory spectral and elemental (±0.3% C, H) or MS analytical data were obtained for all compounds listed in Scheme II.
31. The predominant formation of 2-alkylsilanes from aliphatic 1-olefins has never been observed with any transition-metal catalysts (ref 5).
32. 3-Alkylsilanes, which would be produced by the hydrosilylation of internal olefins formed by isomerization, were not detected.
33. Sharpless, K. B.; Chong, A. O.; Scott, J. A. J. Org. Chem. 1975, 40, 1252.
34. Pikard, R. H.; Kenyon, J. J. Chem. Soc. 1913, 103, 1923.