Rearrangement of 2-(arylmethoxy) methyl-2-oxazolines via lithium azaenolates: a facile synthetic route of ortho-methylmandelic acid derivatives

K Kamata, M Terashima

Index: Kamata, Kazuyuki; Terashima, Masanao Journal of the Chemical Society, Chemical Communications, 1994 , # 24 p. 2771 - 2772

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Abstract

2-(Arylmethoxy)methyl-2-oxazolines, on treatment with LDA in THF at low temperature, rearrange to afford products which are hydrolysed to ortho-methylmandelic acids or a-(l-methyl-2-naphthyl )glycolic acid. ... 2-(Alkoxy)methyl-2-oxazolines, on treatment with LDA in THF at low temperature, give the stable lithium azaenolates, which can react with electrophiles to yield a-substituted products. However, 2-(benzyloxy)methyl-2-oxazoline la, when subjected to ...