Catalytic ring-opening allylation of cyclic acetals with allylsilanes using silica-alumina

Green Chemistry

Volumn 12, Issue 8, 2010, Pages 1373-1375

  Motokura, Ken ^a   Yoneda, Hirokazu ^a   Miyaji, Akimitsu ^a   Baba, Toshihide ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77955208135     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c005033d     Document Type: Article

References (26)

1. M. B. Gravestock D. W. Knight J. S. Lovell S. R. Thornton J. Chem. Soc., Perkin Trans. 1 1999 3143.
2. P. A. Bartlett W. S. Johnson J. D. Elliott J. Am. Chem. Soc. 1983 105 2088.
3. T. Sammakia R. S. Smith J. Org. Chem. 1992 57 2997.
4. S. Bogaczyk M.-R. Brescia Y. C. Shimshock P. DeShong J. Org. Chem. 2001 66 4352.
5. G. K. Friestad H. J. Lee, Org. Lett. 2009 11 3958.
6. Y. Egami M. Takayanagi K. Tanino I. Kuwajima Heterocycles 2000 52 583.
7. W. S. Johnson P. H. Crackett J. D. Elliott J. J. Jagodzinski S. D. Lindell S. Natarajan Tetrahedron Lett. 1984 25 3951.
8. Y. Yamamoto S. Nishii J.-i. Yamada J. Am. Chem. Soc. 1986 108 7116.
9. S. E. Denmark N. G. Almstead J. Am. Chem. Soc. 1991 113 8089.
10. S. E. Denmark N. G. Almstead J. Org. Chem. 1991 56 6458.
11. T. Sammakia R. S. Smith J. Am. Chem. Soc. 1992 114 10998.
12. S. Jiang G. E. Agoston T. Chen M.-P. Cabal E. Turos Organometallics 1995 14 4697.
13. F. Carrel S. Giraud O. Spertini P. Vogel Helv. Chim. Acta 2004 87 1048.
14. M. J. Spafford J. E. Christensen M. G. Huddle J. R. Lacey R. S. Mohan Aust. J. Chem. 2008 61 419.
15. T. Kawabata M. Kato T. Mizugaki K. Ebitani K. Kaneda Chem. Lett. 2003 32 648.
16. M. Barbero S. Cadamuro S. Dughera P. Venturello Synthesis 2008 1379.
17. M. van der Linden J. Borsboom F. Kaspersen G. Kemperman Eur. J. Org. Chem. 2008 2989.
18. R. Tacke T. Schmid M. Penka C. Burschka W. Bains J. Warneck Organometallics 2004 23 4915.
19. The reaction scarcely proceeded with 1-hexene instead of allyltrimethylsilane under the same reaction conditions as in Table 1, entry 1 except for the alkene substrate.
20. G. Crépeau V. Montouillot A. Vimont L. Mariey T. Cseri F. Maugé J. Phys. Chem. B 2006 110 15172.
21. 2 (Table 1, entry 17), mesoporous silica FSM-16 showed 18% yield of the product (entry 11). Effects of mesoporous structure on acid-catalyzed reactions have been reported in the following literature: M. Iwamoto Y. Tanaka N. Sawamura S. Namba J. Am. Chem. Soc. 2003 125 13032.
22. H. Ishitani H. Naito M. Iwamoto Catal. Lett. 2008 120 14.
23. A. Kumar M. Dixit S. P. Singh R. Raghunandan P. R. Maulik A. Goel Tetrahedron Lett. 2009 50 4335.
24. S. G. Rha S.-K. Chang J. Org. Chem. 1998 63 2357.
25. K. Ebitani T. Kawabata K. Nagashima T. Mizugaki K. Kaneda Green Chem. 2000 2 157.
26. After the hydrolysis reaction, reuse of the silica-alumina catalyst was examined. The used silica-alumina was separated from the reaction mixture, then calcined at 500 °C. The catalytic activity of the used catalyst for ring-opening allylation decreased compared with fresh silica-alumina (yield of 3: 83% for 8 h (fresh), 52% for 8 h (reused)). However, after the prolonged reaction time, a satisfactory yield of 3 was obtained (73% for 20 h). Hydrolysis of 3 also proceeded with the used catalyst to afford 5 in 70% yield based on 1.