Stereocontrolled Disruption of the Ugi Reaction toward the Production of Chiral Piperazinones: Substrate Scope and Process Development
详细信息 查看全文
- 作者：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
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：November 7, 2014
- 年：2014
- 卷：79
- 期：21
- 页码：9948-9957
- 全文大小：477K
- ISSN：1520-6904
文摘
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, 伪-amino acids, and monofunctional aldehydes.