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Enantioselective isomerization of allylamine to enamine: practical asymmetric synthesis of (–)-menthol by Rh–BINAP catalysts

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Abstract

Enantioselective isomerizations of allylamines to enamines are summarized from idea to industry. The Rh–BINAP catalyst reveals high selectivities, 99% yield and 98% enantiomer excess and high activity, TON > 400,000. Its industrial use for the production of a 1,500 t/y scale of (–)-menthol is introduced emphasizing technical development.

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  1. Takasago International Corporation, 3–19–22, Takanawa Minato–ku, Tokyo, 108, Japan

    Susumu Akutagawa

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  1. Susumu Akutagawa
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Akutagawa, S. Enantioselective isomerization of allylamine to enamine: practical asymmetric synthesis of (–)-menthol by Rh–BINAP catalysts. Topics in Catalysis 4, 271–274 (1997). https://doi.org/10.1023/A:1019112911246

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  • DOI: https://doi.org/10.1023/A:1019112911246

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