Abstract
Stereoselective Protonation of Carbanions, 6[1]. — Enantioselective Protonation of γ‐Butyrolactone Enolates*The lithium enolates 3Li–7Li, produced from 3–7 by LDA or LiHMDS in THF, are protonated with eleven chiral proton sources at ‐78°C in THF which produced high enantioselectivities with 1Li and 2Li[5]. Although the enolates (3Li, 6Li, 7Li) are not deuterated quantitatively[1], 1H‐ and 13C‐NMR spectra in THF at ‐78°C reveal not only quantitative deprotonation (3Li, 6Li) but also aggregation (dimerisation) and hindered rotation of the phenyl group in 3Li. From comparison of the enantioselectivities produced by five chiral proton sources with 1Li–6Li (Tab. 4) definite structure/selectivity correlations can not be derived both for the enolates and the proton sources.
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