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A solvent‐regulated diastereodivergent [3 + 2] annulation reaction between Morita‐Baylis‐Hillman carbonates from aryl trifluoromethyl ketones and cyclic sulfonimines is developed under the catalysis of a modified cinchona alkaloid, furnishing diverse polycyclic products bearing vicinal quaternary stereogenic centers with outstanding enantioselectivity and moderate to high diastereoselectivity.
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