Abstract
trans-2,5-Disubstituted tetrahydrofurans were obtained as major diastereomers (trans/cis ratio 90:10-100:0) when acetylated gamma-lactols derived from (S)-glutamic acid were treated with titanium enolates of N-acetyl (R)-oxazolidin-2-thiones. A simple transesterification allowed us to obtain the corresponding methyl esters and recover the chiral auxiliary.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetylation
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Esterification
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Furans / chemical synthesis*
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Glutamic Acid / chemistry
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Lactones / chemistry
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Organometallic Compounds / chemistry
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Oxazolidinones / chemistry
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Stereoisomerism
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Titanium / chemistry
Substances
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Furans
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Lactones
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Organometallic Compounds
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Oxazolidinones
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Glutamic Acid
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Titanium