Kwok Sen Wai, Zhang Li, Grimster Neil P, Fokin Valery V
Angew Chem Int Ed Engl. 2014 Mar 24;53(13):3452-6. doi: 10.1002/anie.201306706.
A convenient one-pot asymmetric synthesis of 2,3-dihydropyrroles from in situ generated triflated triazoles and olefins is described that further expands the utility of azavinyl carbene chemistry and provides access to an important class of cyclic enamides. Mechanistic investigations support the involvement of triflated cyclopropylaldimine intermediates in the formation of 2,3-dihydropyrrole. To the best of our knowledge, this is the first example of a chiral Brønsted acid catalyzed rearrangement of cyclopropylimines into enantioenriched 2,3-dihydropyrroles.
本文描述了一种便捷的一锅法不对称合成方法，可从原位生成的三氟甲磺酸化三唑和烯烃制备2,3-二氢吡咯，该方法进一步拓展了氮杂乙烯基卡宾化学的应用，并提供了一种获得重要环状烯酰胺类化合物的途径。机理研究表明，三氟甲磺酸化环丙基亚胺中间体参与了2,3-二氢吡咯的形成过程。据我们所知，这是手性布朗斯特酸催化环丙基亚胺重排为对映体富集的2,3-二氢吡咯的首例报道。
