不对称氮杂-[3+3]环化反应在吲哚里嗪类化合物的合成中的应用：区域化学的意外反转。
Asymmetric aza-[3+3] annulation in the synthesis of indolizidines: an unexpected reversal of regiochemistry.
机构信息
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.
出版信息
Org Lett. 2011 Aug 19;13(16):4402-5. doi: 10.1021/ol2017438. Epub 2011 Jul 25.
Abstract
An enantioselective and diastereoselective aza-[3+3] annulation of pyrrolidine-based exo-cyclic vinylogous amides and urethanes with chiral vinyl iminium salts is described. This asymmetric annulation manifold is possible because of an unexpected regiochemical reversal whereby head-to-tail annulations dominated over the predicted head-to-head. It should find prevalent synthetic applications in the enantioselective synthesis of indolizidines.
摘要
描述了基于吡咯烷的外环乙烯基酰胺和尿烷与手性乙烯亚胺盐的对映选择性和非对映选择性氮杂-[3+3]环化反应。这种不对称环化反应是可能的，因为出乎意料的区域化学反转，其中头对头环化反应为主导，而不是预测的头对头环化反应。它应该在吲哚嗪的对映选择性合成中得到广泛的应用。
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