A Chiral Primary Amine Thiourea Catalyst for the Highly Enantioselective Direct Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes


  • This work was supported by the NIH (GM-43214 and P50 GM069721). M.P.L. gratefully acknowledges the NSERC and La Fondation Baxter et Alma Ricard for graduate scholarships. Dr. Richard Staples is acknowledged for the determination of the crystal structure of 22.


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Dual activation: The bifunctional primary amine thiourea catalyst 1 promotes the highly enantioselective direct conjugate addition of α-branched aldehydes to nitroalkenes (see scheme). Cooperative activation of both the nucleophile and electrophile allows the use of mild reaction conditions and provides access to a wide variety of adducts with vicinal quaternary and tertiary stereogenic centers (>90 % ee).