路易斯酸催化的烯酮亚胺与给体-受体环丙烷的[3 + 2]环化反应：一种合成2-亚烷基吡咯烷衍生物的方法。
Lewis acid catalyzed [3 + 2] annulation of ketenimines with donor-acceptor cyclopropanes: an approach to 2-alkylidenepyrrolidine derivatives.
作者信息
Alajarin Mateo, Egea Adrian, Orenes Raul-Angel, Vidal Angel
机构信息
Departamento de Química Orgánica, Universidad de Murcia, Facultad de Química, Regional Campus of International Excellence "Campus Mare Nostrum", Espinardo, 30100 Murcia, Spain.
Servicio Universitario de Instrumentación Científica, Universidad de Murcia, Regional Campus of International Excellence "Campus Mare Nostrum", Espinardo, 30100, Murcia, Spain.
出版信息
Org Biomol Chem. 2016 Nov 2;14(43):10275-10284. doi: 10.1039/c6ob02005d.
The [3 + 2] annulation reaction of C,C,N-trisubstituted ketenimines with donor-acceptor cyclopropanes bearing aryl, styryl and vinyl substituents at the C2 position, triggered by the Lewis acid Sc(OTf), supplies highly substituted pyrrolidines. Activated cyclopropanes fused to naphthalene and [1]benzopyrane nuclei are also suitable substrates in similar transformations, yielding partially saturated benz[g]indoles and [1]benzopyran[4,3-b]pyrroles. An intramolecular version of this ketenimine/cyclopropane [3 + 2] annulation has also been developed leading to the pyrrolo[2,1-a]isoindole framework.
在路易斯酸三氟甲磺酸钪（Sc(OTf)₃）引发下，C,C,N-三取代烯酮亚胺与在C2位带有芳基、苯乙烯基和乙烯基取代基的给体-受体环丙烷发生的[3 + 2]环化反应，可提供高度取代的吡咯烷。与萘和[1]苯并吡喃核稠合的活化环丙烷也是类似转化中的合适底物，可生成部分饱和的苯并[g]吲哚和[1]苯并吡喃[4,3 - b]吡咯。这种烯酮亚胺/环丙烷[3 + 2]环化反应的分子内版本也已开发出来，可得到吡咯并[2,1 - a]异吲哚骨架。
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