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Stereoselectivity of Proline/Cyclobutane Amino Acid-Containing Peptide Organocatalysts for Asymmetric Aldol Additions: A Rationale

Illa, Ona ; Porcar-Tost, Oriol ; Robledillo, Carme ; Elvira, Carlos ; Nolis, Pau ; Reiser, Oliver ; Branchadell, Vicenç ; Ortuño, Rosa M.


Several alpha,beta,alpha- or alpha,gamma,alpha-tripeptides, consisting of a central cyclobutane beta- or gamma-amino acid being flanked by two D- or L-proline residues, have been synthesized and tested as organocatalysts in asymmetric aldol additions. High yields and enantioselectivities have been achieved with alpha,gamma,alpha-tripeptides, being superior to peptides containing a cydobutane ...


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