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Rh(III)-Catalyzed Diastereodivergent Spiroannulation of Cyclic Imines with Activated Alkenes.

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Rh(III)-catalyzed [3 + 2] annulation of cyclic N-sulfonyl or N-acyl ketimines with activated alkenes has been realized, leading to the synthesis of spirocycles with three continuous stereogenic centers. This atom-economic… Click to show full abstract

Rh(III)-catalyzed [3 + 2] annulation of cyclic N-sulfonyl or N-acyl ketimines with activated alkenes has been realized, leading to the synthesis of spirocycles with three continuous stereogenic centers. This atom-economic reaction proceeded efficiently under mild and redox-neutral conditions via a C-H activation pathway, and the coupling is diastereodivergent, with the diastereoselectivity being controlled by silver additives.

Keywords: spiroannulation cyclic; catalyzed diastereodivergent; diastereodivergent spiroannulation; cyclic imines; iii catalyzed; activated alkenes

Journal Title: Organic letters
Year Published: 2017

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