| Autor: |
Zaretsky S; Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario M5S 3H6, Canada., Adachi S, Rotstein BH, Hickey JL, Scully CC, St Denis JD, Courtemanche R, Yu JC, Chung BK, Yudin AK |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2014 Nov 07; Vol. 79 (21), pp. 9948-57. Date of Electronic Publication: 2014 Oct 22. |
| DOI: |
10.1021/jo5018316 |
| Abstrakt: |
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. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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