- Merging α-Lithiation and Aldol-Tishchenko Reaction to Construct Polyols from Benzyl Ethers
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α-Lithiobenzyl ethers, generated by selective α-lithiation, undergo an aldol-Tishchenko reaction upon treatment with carboxylic esters and paraformaldehyde. The reaction of the organolithium with the carboxylate generates an intermediate enolate that, after formaldehyde addition, affords 1,2,3-triol derivatives in a straightforward and one-pot manner. These products are obtained as single diastereoisomers bearing a quaternary stereocenter. The complete diastereocontrol of the aldol-Tishchenko process is attributed to stereoelectronic preferences in the transition state.
- Sedano, Carlos,Velasco, Rocío,Suárez-Pantiga, Samuel,Sanz, Roberto
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Read Online
- Direct metalation of methoxymethyl arylmethyl ethers: A tin-free approach to the generation of α-alkoxyalkoxy-substituted aryllithiums
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The generation of a series of α-methoxymethoxy-substituted arylmethyllithiums was achieved by direct metalation of the corresponding arylmethyl methoxymethyl ethers. While the effect of substituents at the benzylic position is straightforward, substituent
- Azzena, Ugo,Pisano, Luisa,Mocci, Sarah
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experimental part
p. 3619 - 3625
(2010/01/18)
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