Prieto Liher, Juste-Navarro Veronica, Uria Uxue, Delso Ignacio, Reyes Efraim, Tejero Tomas, Carrillo Luisa, Merino Pedro, Vicario Jose L
Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080, Bilbao, Spain.
Laboratorio de Síntesis Asimétrica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza-CSIC, Campus San Francisco, 5009, Zaragoza, Spain.
Chemistry. 2017 Feb 24;23(12):2764-2768. doi: 10.1002/chem.201605350. Epub 2017 Feb 7.
The reaction of nitrones with enals through iminium activation can be modulated by using cooperative hydrogen-bonding catalysis to induce the participation of a nitrone ylide (C-N-C) instead of the classical C-N-O dipole. As a consequence, N-hydroxypyrrolidines are obtained, rather than the expected isoxazolidines. The reaction proceeds smoothly and high enantioselectivities are observed in all cases. By using the appropriate substrate, polysubstituted pyrrolidines incorporating quaternary stereocenters can be efficiently prepared.
通过亚胺离子活化，利用协同氢键催化诱导硝酮叶立德（C-N-C）而非经典的C-N-O偶极子参与反应，可调控硝酮与烯醛的反应。结果得到的是N-羟基吡咯烷，而非预期的异恶唑烷。该反应顺利进行，在所有情况下均观察到高对映选择性。通过使用合适的底物，可以高效制备含有季碳立体中心的多取代吡咯烷。
