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| - Reverse Turn Induced π-Facial Selectivity duringPolyaniline-Supported Cobalt(II) Salen Catalyzed AerobicEpoxidation of N-Cinnamoyl l-Proline Derived Peptides
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| - A novel chemo- and diastereoselective aerobic epoxidation of the N-cinnamoyl peptides catalyzedby polyaniline-supported cobalt(II) salen (PASCOS) is described. The N-cinnamoyl proline derivedpeptides 1 show a high π-facial selectivity during these epoxidations. The origin of this diastereoselectivity in 1 has been attributed to (i) the propensity of the N-cinnamoyl proline amide to existpredominantly as trans rotamer in CDCl3, DMSO-d6, and CH3CN medium and (ii) existence ofthese peptides as organized structures (γ- and β-turns) due to the presence of intramolecularhydrogen bonds. An extensive solution NMR and MD simulation study on 1d and 1f indicates thatthe origin of the high π-facial selectivity is due to the well-defined γ- and β-turns which result inthe hindrance of one face of the cinnamoyl double bond in the transition state of the epoxidationreaction.
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