Abstract
[reaction: see text] An enantioselective synthetic method for alpha-alkylserines by the phase-transfer catalytic alkylation of 2-phenyl-2-oxazoline-4-carbonylcamphorsultam (4a) was developed. The phase-transfer catalytic alpha-alkylation of 4a using P2-Et at -78 degrees C gave alpha-alkylation (75 to approximately 99%, 90 to approximately 97% de), which could be easily hydrolyzed to alpha-alkylserines.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkylation
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Carboxylic Acids / chemistry
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Esters / chemistry
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Eugenol / analogs & derivatives*
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Eugenol / chemistry*
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Models, Chemical
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Oxazoles / chemistry*
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Serine / analogs & derivatives*
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Serine / chemical synthesis
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Serine / chemistry
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Stereoisomerism
Substances
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2-phenyl-2-oxazoline-4- carbonylcamphorsultam
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2-phenyl-2-oxazoline-4-carboxylic acid tert-butyl ester
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Carboxylic Acids
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Esters
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Oxazoles
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Eugenol
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Serine