- Syn-β-hydroxyallylic silanes from terminal epoxide α-lithiation-silylation and alkenylation: Application to the tetrahydrofuran portion of the lytophilippines
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Lithiation-in situ silylation of terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide in combination with phenyldimethyl(or diethyl)silyl chloride provides a direct process for the synthesis of trans-α,β-epoxysilanes, which undergo α-ring opening with alkenylcoppers to give syn-β-hydroxyallylic silanes. The chemistry is applied in an annulation approach to the C10-C19 tetrahydrofuran-containing portion of the lytophilippines.
- Hodgson, David M.,Salik, Saifullah
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supporting information
p. 4402 - 4405
(2012/11/06)
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- Stereospecific Rearrangement of 2,2-Disubstituted Vinylsilane Epoxides to the Silyl Enol Ethers of 2,2-Disubstituted Aldehydes
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The Z- and E-2-ethyl-2-methylvinylsilane epoxides (5a) and (5b) rearrange stereospecifically in the presence of boron trifluoride-diethyl ether to the Z- and E-silyl enol ethers, (6a) and (6b), respectively, of 2-methylbutanal.These silyl enol ethers reac
- Fleming, Ian,Newton, Trevor W.
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p. 119 - 124
(2007/10/02)
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