Novel Synthesis of Optically Active 2??Ethylhexanoic Acid, 2??Ethylhexanol, and 2??Ethylhexylamine via the Asymmetric Favorskii Rearrangement

M Miura, M Toriyama, S Motohashi

Index: Miura, Motofumi; Toriyama, Masaharu; Motohashi, Shigeyasu Synthetic Communications, 2006 , vol. 36, # 3 p. 259 - 264

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Citation Number: 5

Abstract

Abstract The asymmetric Favorskii rearrangement of optically active α??haloketones, which are easily prepared from chiral menthyl??4??toluenesulfoxide in several steps using primary or secondary amines, yields their corresponding secondary or tertiary chiral amides. The secondary chiral amides were converted to acids or amines using acylation followed by hydrolysis or reduction. In addition, the tertiary amides were directly reduced to alcohol ...