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Synthesis via oxazolines. VI. An asymmetric synthesis of β-hydroxy and β-methoxy alkanoic acids

✍ Scribed by A.I. Meyers; Gerald Knaus

Book ID
104234811
Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
165 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis

The recently reported asymmetric synthesis of a-methyl alkanoic acids utilizing chiral non-racemic oxazolines' has prompted further studies in an effort to evaluate their full synthetic potential. The e-methyl oxazoline l2 was readily obtained from commercially available lS,2S-(+)-1-phenyl-2-amino-1,3-propane diol k3 and the ethyl imidate hydrochloride of acetonitrile4 by stirring in dichloromethane (O", 6h), followed by ether formation using sodium hydride-methyl iodide. Treatment of lwith 1.0 equiv of n-butyllithium (THF, -78') produced, after a few minutes, a yellow suspension, which is presumed to be the lithio salt 2'

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