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Stereocontrolled Disruption of the Ugi Reaction toward the Production of Chiral Piperazinones: Substrate Scope and Process Development

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posted on 07.11.2014, 00:00 authored by Serge Zaretsky, Shinya Adachi, Benjamin H. Rotstein, Jennifer L. Hickey, Conor C. G. Scully, Jeffrey D. St. Denis, Rebecca Courtemanche, Joy C. Y. Yu, Benjamin K. W. Chung, Andrei K. Yudin
The factors determining diastereoselectivity observed in the multicomponent conversion of amino acids, aziridine aldehyde dimers, and isocyanides into chiral piperazinones have been investigated. Amino acid-dependent selectivity for either trans- or cis-substituted piperazinone products has been achieved. An experimentally determined diastereoselectivity model for the three-component reaction driven by aziridine aldehyde dimers has predictive value for different substrate classes. Moreover, this model is useful in reconciling the previously reported observations in multicomponent reactions between isocyanides, α-amino acids, and monofunctional aldehydes.