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The Stereochemistry of simple enols in solution

โœ Scribed by Brian Capon; Arup K. Siddhanta


Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
162 KB
Volume
23
Category
Article
ISSN
0040-4039

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Deprotonation of methyl phenylacetate with lithium diisopropylamide in tetrahydrofuran followed by trapping with trimethylsilyl chloride afforded an 81:19 mixture of E-and Z-silyl ketene acetals in agreement with a prediction by the calculation by Dauben. The E-silyl ketene acetal was readily isomet

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It was found that in tetrahydrofuran solution, predominance (99.2%) of the highly stabilized Meyers enolate (1,5-dimethylpyrrolidin-2-one lithium enolate (1)) isomer with intramolecular Li-p C C coordination from the endo-face (Ct-endo) may be responsible for exceedingly high endo-selectivity in Mey