Direct organocatalytic asymmetric Mannich-type reactions in aqueous media: one-pot Mannich-allylation reactions |
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Authors: | Armando CórdovaCarlos F Barbas III |
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Institution: | Skaggs Institute for Chemical Biology and Department of Molecular Biology, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA |
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Abstract: | The first direct organocatalytic asymmetric Mannich-type reactions in aqueous media are demonstrated herein. l-Proline-catalyzed reactions in aqueous media to provide β-formyl substituted α-amino acid derivatives with excellent diastereoselectivities (dr up to 19:1, syn/anti) and high enantioselectivities (ee between 72 and >99%). These conditions provided for the development of novel one-pot asymmetric syntheses of cyclic γ-allyl substituted α-amino acid derivatives (ee up to >99%). This was accomplished by combining the proline-catalyzed Mannich-type reactions with indium promoted allylations in aqueous media. |
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