Novel reactions of ethylene acetals with silyl-substituted nucleophiles. A mild and efficient procedure for the synthesis of homoallyl alkyl ethers and unsymmetrical dialkyl ethers

Synthetic Communications

Volumn 29, Issue 8, 1999, Pages 1263-1269

  Suzuki, Takeshi ^a   Oriyama, Takeshi ^a  

^a IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALKYL ETHER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY; SYNTHESIS;

EID: 0032936383     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919908086101     Document Type: Article

References (20)

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10. We have reported the novel synthesis of cyclic ethers by the allylation of acetals, see: (a) Oriyama, T.; Ishiwata, A.; Sano, T.; Matusda, T.; Takahashi, M.; Koga, G. Tetrahedron Lett. 1995, 36, 5581.
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15. 3) δ 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.
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17. (b) Olah, G. A.; Yamato, T.; Iyer, P. S.; Prakash, G. K. S., J. Org. Chem. 1986, 51, 2826.
18. Using triethylsilane in place of t-butyldimethylsilane, the yield of the coressponding dialkyl ethers decreased by 5-20%.
19. For reaction of carbonyl compounds with trialkylsilane to afford unsymmetrical ethers in the presence of alcohol variants, see: (a) Doyle, M. P.; DeBruyn, D. J.; Kooista, D. A. J. Am. Chem. Soc. 1972, 94, 3659.
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