Stereoselective allylation of acetals through intramolecular transfer of an allylsilane

Organic Letters

Volumn 1, Issue 6, 1999, Pages 917-919

  Fujita, Kazuya ^a   Inoue, Atsushi ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001744676     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990840m     Document Type: Article

References (27)

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16. Enantioselective syntheses of homoallylic ethers via alkyl silyl mixed acetal intermediate have been reported; see: Tietze, L. F.; Wulff, C.; Wegner, C.; Schuffenhauer, A.; Schiemann, K. J. Am. Chem. Soc. 1998, 120, 4276. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1998, 4, 1862. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1996, 2, 1164. Tietze, L. F.; Dölle, A.; Schiemann, K. Angew. Chem., Int Ed. Engl. 1992, 31, 1372. Tietze, L. F.; Schiemann, K.; Wegner, C. J. Am. Chem. Soc. 1995, 117, 5851. Mukaiyama, T.; Ohshima, M.; Miyoshi, N. Chem. Lett. 1987, 1121.
17. Enantioselective syntheses of homoallylic ethers via alkyl silyl mixed acetal intermediate have been reported; see: Tietze, L. F.; Wulff, C.; Wegner, C.; Schuffenhauer, A.; Schiemann, K. J. Am. Chem. Soc. 1998, 120, 4276. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1998, 4, 1862. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1996, 2, 1164. Tietze, L. F.; Dölle, A.; Schiemann, K. Angew. Chem., Int Ed. Engl. 1992, 31, 1372. Tietze, L. F.; Schiemann, K.; Wegner, C. J. Am. Chem. Soc. 1995, 117, 5851. Mukaiyama, T.; Ohshima, M.; Miyoshi, N. Chem. Lett. 1987, 1121.
18. Enantioselective syntheses of homoallylic ethers via alkyl silyl mixed acetal intermediate have been reported; see: Tietze, L. F.; Wulff, C.; Wegner, C.; Schuffenhauer, A.; Schiemann, K. J. Am. Chem. Soc. 1998, 120, 4276. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1998, 4, 1862. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1996, 2, 1164. Tietze, L. F.; Dölle, A.; Schiemann, K. Angew. Chem., Int Ed. Engl. 1992, 31, 1372. Tietze, L. F.; Schiemann, K.; Wegner, C. J. Am. Chem. Soc. 1995, 117, 5851. Mukaiyama, T.; Ohshima, M.; Miyoshi, N. Chem. Lett. 1987, 1121.
19. Enantioselective syntheses of homoallylic ethers via alkyl silyl mixed acetal intermediate have been reported; see: Tietze, L. F.; Wulff, C.; Wegner, C.; Schuffenhauer, A.; Schiemann, K. J. Am. Chem. Soc. 1998, 120, 4276. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1998, 4, 1862. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1996, 2, 1164. Tietze, L. F.; Dölle, A.; Schiemann, K. Angew. Chem., Int Ed. Engl. 1992, 31, 1372. Tietze, L. F.; Schiemann, K.; Wegner, C. J. Am. Chem. Soc. 1995, 117, 5851. Mukaiyama, T.; Ohshima, M.; Miyoshi, N. Chem. Lett. 1987, 1121.
20. Enantioselective syntheses of homoallylic ethers via alkyl silyl mixed acetal intermediate have been reported; see: Tietze, L. F.; Wulff, C.; Wegner, C.; Schuffenhauer, A.; Schiemann, K. J. Am. Chem. Soc. 1998, 120, 4276. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1998, 4, 1862. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1996, 2, 1164. Tietze, L. F.; Dölle, A.; Schiemann, K. Angew. Chem., Int Ed. Engl. 1992, 31, 1372. Tietze, L. F.; Schiemann, K.; Wegner, C. J. Am. Chem. Soc. 1995, 117, 5851. Mukaiyama, T.; Ohshima, M.; Miyoshi, N. Chem. Lett. 1987, 1121.
21. Enantioselective syntheses of homoallylic ethers via alkyl silyl mixed acetal intermediate have been reported; see: Tietze, L. F.; Wulff, C.; Wegner, C.; Schuffenhauer, A.; Schiemann, K. J. Am. Chem. Soc. 1998, 120, 4276. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1998, 4, 1862. Tietze, L. F.; Schiemann, K.; Wegner, C.; Wulff, C. Chem. Eur. J. 1996, 2, 1164. Tietze, L. F.; Dölle, A.; Schiemann, K. Angew. Chem., Int Ed. Engl. 1992, 31, 1372. Tietze, L. F.; Schiemann, K.; Wegner, C. J. Am. Chem. Soc. 1995, 117, 5851. Mukaiyama, T.; Ohshima, M.; Miyoshi, N. Chem. Lett. 1987, 1121.
22. Shinokubo, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1997, 70, 2255.
23. 4NF, a hydroxydiphenylsilyl ether of allylic alcohol 4a or 4b was observed in the crude mixture.
24. 3SiOTf, see ref 4b.
25. 4Cl, and the whole was extracted with ether. The combined organic extracts were concentrated in vacuo, and the residue was dissolved in methanol. To this was added two drops of concentrated HCl, and the mixture was stirred for 1 h. Extractive workup followed by purification by silica gel column chromatography afforded anti-6-hexyl-7-octene-1,5-diol (0.12 g, 0.52 mmol) in 61% yield.
26. The preexisting stereogenic center of 8c and 8f seems to have no influence on the stereoselectivity of the reaction (entries 3 and 6). For instance, the isomeric ratio of 8c (60/40) was maintained throughout the reaction and 9c was obtained as a mixture of two anti-1,4-diols (60/40).
27. The reason for the moderate selectivity in Z-isomer is not clear at this stage. A reviewer suggested a possible explanation as follows. The trichloromethyl group is quite large and its steric hindrance would make reaction through a cyclic transition state unfavorable in the case of the Z isomer.