Organic Letters 2012-03-02

Catalytic enantioselective desymmetrization of meso-glutaric anhydrides using a stable Ni2-Schiff base catalyst.

Purushothaman Gopinath, Takumi Watanabe, Masakatsu Shibasaki

Index: Org. Lett. 14(5) , 1358-61, (2012)

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Abstract

We describe the desymmetrization of meso-glutaric anhydrides to chiral hemiesters using a bench-stable homodinuclear Ni(2)-(Schiff base) complex as the catalyst in good to excellent yield (up to 99%) and enantioselectivity (up to 94%). Using the opposite enantiomer of the catalyst, we obtained the same yield and enantioselectivity with the opposite configuration, thereby gaining access to both hemiester enantiomers.© 2012 American Chemical Society