Abstract
A [1,5]-anion relay has been achieved in 3,3-bis(silyl) benzyl enol ether. Deprotonation at the sterically more accessible benzyl position triggers an intramolecular proton transfer to generate the thermodynamically more stable 3,3-bis(silyl) allyloxy lithium. This endo-oriented allyl anion is stable at -78 °C and undergoes diastereoselective syn-addition at the γ-position with aldehydes and ketones to give monobenzyl-substituted 1,2-diols.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry*
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Anions / chemistry
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Ethers / chemistry
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Ketones / chemistry*
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Lithium / chemistry*
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Molecular Structure
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Organometallic Compounds / chemical synthesis*
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Organometallic Compounds / chemistry
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Protons*
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Silanes / chemical synthesis*
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Silanes / chemistry
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Stereoisomerism
Substances
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Aldehydes
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Anions
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Ethers
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Ketones
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Organometallic Compounds
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Protons
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Silanes
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Lithium