Asymmetric α-Alkylation of Phenylacetates Using 2-Alkylamino-2′-hydroxy-1,1′-binaphthyls as Chiral Auxiliaries

Masato Kawamura Institute of Industrial Science, The University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo, 153-8505, Japan

Takashi Kurahashi Institute of Industrial Science, The University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo, 153-8505, Japan

Shinsaku Shiraishi Institute of Industrial Science, The University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo, 153-8505, Japan

Kazuaki Kudo Institute of Industrial Science, The University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo, 153-8505, Japan

-Alkylation of 2-phenylacetate ester of 2-alkylamino-2'-hydroxy-1,1'-binaphthyls with various alkyl iodides proceeded with good stereoselectivities. An intramolecular hydrogen bonding between N-H group and the carbonyl oxygen seemed to play an important role for asymmetric induction. The auxiliary was also applicable to Diels-Alder reaction of an acrylate.

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Asymmetric α-Alkylation of Phenylacetates Using 2-Alkylamino-2′-hydroxy-1,1′-binaphthyls as Chiral Auxiliaries

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Asymmetric α-Alkylation of Phenylacetates Using 2-Alkylamino-2′-hydroxy-1,1′-binaphthyls as Chiral Auxiliaries

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