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LiAlH 4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(−)-2-(2-isoindolinyl)butan-1-ol 1 reduced the six α-aminophenones 4–9 into the corresponding optically active β-aminoalcohols 10–15 whose ee's were in the range 40–97% after chromatography and recrystallization. The asymmetric reduction of the ortho-dimethylaminobenzophenone 18, using the same reducing agents afforded the enantiomerically...
Treatment of the readily available (S)-(+) and (R)-(-) enantiomers of 2-aminobutan-1-ol 1 with sodium hydride followed by benzyl chloride, or a substituted benzyl halide, afforded the corresponding O-benzyl bases 4-7 in good yields. These new bases are recommended for the large scale resolution of racemic acids. For instance, they proved efficient for the practical resolutions of α-methylsuccinic...
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