Regioselective synthesis and acylation of cyclic bis-(trimethylsiloxy)- 1,3-dienes - New and versatile 1,3-dianion synthons

Synlett

Volumn , Issue 4, 2000, Pages 497-500

  Langer, Peter ^a   Schneider, Toni ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Bis (trimethylsiloxy) 1,3 dienes; Rearrangements; Regioselectivity; Silyl enol ethers; Synthetic methodology

Indexed keywords

ALKADIENE; ETHER DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034111188     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

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20. 4), filtered and the solvent of the filtrate was removed in vacuo. The residue was purified by column chromatography (silica gel, ether / petrol ether). Most dienes were obtained as a single geometric isomer the configurations of which were tentatively assigned based on steric considerations. All new compounds were characterized spectroscopically and gave correct elemental analyses and/ or high resolution mass data.
21. 4-mediated acetylations, see: Chan, T. H.; Stössel, D., J. Org. Chem. 1986, 51, 2423. For the use of TMSOTf in reactions with other electrophiles, see ref. 5(e).
22. ++1).
23. a) Krägeloh, K.; Simchen, G., Synthesis 1981, 30;
24. b) Langer, P.; Schneider, T., unpublished results.
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27. For a related rearrangement, see: Anderson, G.; Cameron, D. W.; Feutrill, G. I.; Read, R. W., Tetrahedron Lett. 1981, 22, 4347.
28. 3SiCl in an attempt to prepare the corresponding bis-(trimethylsiloxy)-1,3-diene: P. Langer, T. Schneider, unpublished results.