A Concise Asymmetric Route to Chiral alpha-Aminoxy Acids

[摘要]：An efficient three-step method has been developed for enantioselective synthesis of chiral alpha-aminoxy acids from aldehydes. In this method, chiral propargylic alcohols are obtained by asymmetric addition of terminal alkynes to aldehydes. The hydroxyl group then converted to aminoxy group via Mitsunobu reaction and oxidative cleavage of the internal carbon-carbon triple bond produce the carboxylic acid group. This represents a convenient approach to the general asymmetric synthesis of alpha-aminoxy acids with the advantages of substantial overall yields (37-73%) and high enantioselectivities (81-99% ee).

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