References
- Hosomi , A. and Sakurai , H. 1976 . Tetrahedron Lett. , 17 : 1295
- Sakurai , H. 1982 . Pure Appl. Chem. , 54 : 1
- Davis , A. P. and Jaspars , M. 1990 . J. Chem. Soc, Chem. Commun. , : 1176
- Hosomi , A. 1998 . Ace. Chem. Res. , 21 : 200
- Hosomi , A. , Endo , M. and Sakurai , H. 1976 . Chem. Lett. , : 941
- Tsunoda , T. , Suzuki , M. and Noyori , R. 1980 . Tetrahedron Lett. , 21 : 71
- Sakurai , H. , Sasaki , K. and Hosomi , A. 1981 . Tetrahedron Lett. , 22 : 745
- Sakurai , H. , Sasaki , K. , Hayashi , J. and Hosomi , A. 1984 . J. Org. Chem. , 49 : 2808
- Mukaiyama , T. , Nagaoka , H. , Murakami , M. and Oshima , M. 1985 . Chem. Lett. , : 977
- Oriyama , T. , Ishiwata , A. , Sano , T. , Matusda , T. , Takahashi , M. and Koga , G. 1995 . Tetrahedron Lett. , 36 : 5581 We have reported the novel synthesis of cyclic ethers by the allylation of acetals, see:
- Oriyama , T. and Sano , T. 1997 . Synlett , : 716
- Jordaan , J. H. and Serfontein , W. J. 1963 . J. Org. Chem. , 28 : 1395
- Tsunoda , T. , Suzuki , M. and Noyori , R. 1980 . Tetrahedron Lett. , 21 : 1357
- Hara , R. , Furukawa , T. , Horiguchi , Y. and Kuwajima , I. 1996 . J. Am. Chem. Soc. , 118 : 9186
- Typical experimental procedure is as follows: To a suspension of anhydrous tin(II) trifluoromethanesulfonate (104.2 mg, 0.25 mmol) and benzyloxy-trimethylsilane (90.2 mg, 0.50 mmol) in CH3CN (2 ml) were added benzaldehyde ethylene acetal (37.5 mg, 0.25 mmol) in CH3CN (1.5 ml) and allyltrimethylsilane (40.0 mg, 0.35 mmol) in CH3CN (1.5 ml) successively at -20 °C under an argon atmosphere. The reaction mixture was stirred for 3 h at -20 °C and quenched with saturated aqueous sodium hydrogen carbonate. The organic materials were extracted with dichloromethane and the combined extracts were washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated and 4-benzyloxy-4-phenyl-l-butene (55.4 mg, 93%) was isolated by thin-layer chromatography on silica gel (ether : hexane = 1:7).1H NMR(400MHz, CDC13) 7.39–7.25 (m, 10H), 5.83–5.72 (m, 1H), 5.05 (d, J = 14.1 Hz, 1H), 5.01 (d, J=9.2 Hz, 1H), 4.46(d, J = 12.0 Hz, 1H), 4.26(d, J= 12.0 Hz, 1H), 2.47–2.41 (m, 1H). 13CNMR(100MHz, CDCl3) 141.8, 138.5, 134.9, 128.4 128.3, 127.7, 127.6, 127.4, 126.9, 116.8, 81.1, 70.3, 42.6
- Tsunoda , T. , Suzuki , M. and Noyori , R. 1979 . Tetrahedron Lett. , 20 : 4679 For reaction of acetals with trialkylsilane, see:
- Olah , G. A. , Yamato , T. , Iyer , P. S. and Prakash , G. K. S. 1986 . J. Org. Chem. , 57 : 2826
- Using triethylsilane in place of t-butyldimethylsilane, the yield of the coressponding dialkyl ethers decreased by 5–20%
- Doyle , M. P. , DeBruyn , D. J. and Kooista , D. A. 1972 . J. Am. Chem. Soc. , 94 : 3659 For reaction of carbonyl compounds with trialkylsilane to afford unsymmetrical ethers in the presence of alcohol variants, see:
- Kato , J. , Iwasawa , N. and Mukaiyama , T. 1985 . Chem Lett. , : 743