Palladium-catalyzed allylic alkylation of optically active α-alkenyl-α-acyloxytrialkylsilane

Tetrahedron Letters

Volumn 46, Issue 30, 2005, Pages 5009-5012

  Sakaguchi, Kazuhiko ^a   Yamada, Takeshi ^a   Ohfune, Yasufumi ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Acyloxysilane; Silyl cation; Chirality transfer; Pd catalyzed allylic alkylation

Indexed keywords

PALLADIUM; SILANE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; MOLECULAR DYNAMICS; STEREOCHEMISTRY;

EID: 20544453835     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.076     Document Type: Article

References (33)

1. K. Sakaguchi, H. Mano, and Y. Ohfune Tetrahedron Lett. 39 1998 4311 4312
2. K. Sakaguchi, M. Fujita, and Y. Ohfune Tetrahedron Lett. 39 1998 4313 4316
3. K. Sakaguchi, M. Fujita, H. Suzuki, M. Higashino, and Y. Ohfune Tetrahedron Lett. 41 2000 6589 6592
4. K. Sakaguchi, H. Suzuki, and Y. Ohfune Chirality 13 2001 357 365
5. Y. Morimoto, M. Takanishi, T. Kinoshita, K. Sakaguchi, and K. Shibata Chem Commun. 2002 42 43
6. K. Sakaguchi, M. Yamamoto, T. Kawamoto, T. Yamada, T. Shinada, T. Shimamoto, and Y. Ohfune Tetrahedron Lett. 45 2004 5869 5872
7. Several reports regarding the stability of α-silyl cation, see: Y. Apeloig, and A. Stanger J. Am. Chem. Soc. 107 1985 2806 2807
8. J.A. Soderquist, and A. Hassner Tetrahedron Lett. 29 1988 1899 1902
9. Y. Apeloig, R. Biton, and A. bu-Freih J. Am. Chem. Soc. 115 1993 2252 2253
10. K. Sakaguchi, M. Higashino, and Y. Ohfune Tetrahedron 59 2003 6647 6658
11. Reviews for Pd-catalyzed allylic alkylations, see: B.M. Trost, and T.R. Verhoeven Comprehensive Organometallic Chemistry Vol. 8 1982 Pergamon Press p 799
12. S.A. Godleski Comprehensive Organic Synthesis Vol. 4 1999 Pergamon Press p 585
13. J. Tsuji Palladium Reagent and Catalysts 2004 John Wiley & Sons Chichester p 431
14. Pd-catalyzed allylic alkylation of silicon-containing substrate, see: T. Hirao, J. Enda, Y. Ohshiro, and T. Agawa Tetrahedron Lett. 22 1981 3079 3080
15. C. Commandeur, S. Thorimbert, and M.J. Malacria Org. Chem. 68 2003 5588 5592
16. 3) δ 5.93 (dd, J = 18.6, 7.4 Hz, 1H), 5.70 (dd, J = 18.6, 0.8 Hz, 1H), 3.72 (s, 3H), 3.67 (s, 3H), 3.33 (d, J = 9.2 Hz, 1H), 2.97 (dqd, J = 9.2, 6.8, 6.8 Hz, 1H), 1.08 (d, J = 6.8, 3H), 0.83 (s, 9H), 0.01 (s, 3H), -0.02 (s, 3H).
17. B.M. Trost, and T.R. Verhoeven J. Am. Chem. Soc. 102 1980 4730 4743
18. C.G. Frost, J. Howarth, and J.M.J. Williams Tetrahedron: Asymmetry 3 1992 1089 1122
19. 2a
20. As a control experiment, the reaction of (R,Z)-1 (>95% ee) using method B without carbon nucleophile resulted in a formation of 1-TBDMS-1,3-butadiene with a recovery of (R,Z)-1 (>95% ee). This also suggests the present reaction proceeds through a π-allyl palladium(II) intermediate in Scheme 3.
21. The (R,Z)-α-acyloxysilane 1 (>95% ee) was converted to (S,E)-vinylsilane 2 (>95% ee) via Pd(II)-catalyzed allylic rearrangement in two steps (67%) by Panek's protocol: J.S. Panek, and M.A. Sparks J. Org. Chem. 55 1990 5564 5566
22. H. Kurosawa, H. Kajimaru, S. Ogoshi, H. Yoneda, K. Miki, N. Kasai, S. Murai, and I. Ikeda J. Am. Chem. Soc. 114 1992 8417 8424
23. Intramolecular Pd-catalyzed allylic alkylation, see: B.M. Trost, and T.R. Verhoeven J. Am. Chem. Soc. 102 1980 4743 4763
24. T. Takahashi, Y. Jinbo, K. Kitamura, and J. Tsuji Tetrahedron Lett. 25 1984 5921 5924
25. K. Yamamoto, R. Deguchi, Y. Ogimura, and J. Tsuji Chem. Lett. 1984 1657 1660
26. B.M. Trost Angew. Chem., Int. Ed. Engl. 28 1989 1173 1192
27. A. Heumann, and M. Reglier Tetrahedron 51 1995 975 1015
28. 3) δ 5.96 (dd, J = 18.6, 7.3 Hz, 1H), 5.71 (dd, J = 18.6, 1.2 Hz, 1H), 3.72 (s, 3H), 3.62 (s, 3H), 3.29 (dt, J = 7.2, 7.2 Hz, 1H), 2.47 (dt, J = 13.7, 8.3 Hz, 1H), 2.08 (ddd, J = 13.8, 9.0, 4.8 Hz, 1H), 1.99-1.81 (2H), 1.75-1.50 (2H), 0.84 (s, 9H), -0.02 (s, 6H).
29. The reaction using a carbonate instead of acetate without a base under the same conditions did not proceed at all, while heating under reflux for 7 h gave diene 5 (34%). The use of 2 equiv of NaH gave a mixture of 4 (24%) and 5 (10%) when heated under reflux for 7 h.
30. 3, or DPPP by-produced the diene 5.
31. 2 (0.05 equiv) (DMF, 100°C, 19 h) gave 5 (32%) with recovery of 3b (56%).
32. 2 gave 4 (72%) as the sole product.
33. 1H NMR.