Korboukh Ilia, Kumar Praveen, Weinreb Steven M
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
J Am Chem Soc. 2007 Aug 29;129(34):10342-3. doi: 10.1021/ja074108r. Epub 2007 Aug 3.
The first examples of intramolecular Michael-type reactions of in situ-formed vinylnitroso compounds with carbon nucleophiles are reported. This methodology has been used to prepare a variety of ring systems including [3.2.1]-, [2.2.2]- and [2.2.1]-bridged carbobicyclic compounds, as well as a fused [5.5]-ring compound. Malonate anions have proven to be effective carbon nucleophiles in these conjugate addition reactions, and simple ester potassium enolates have also been successfully employed.
报道了原位形成的乙烯基亚硝基化合物与碳亲核试剂的分子内迈克尔型反应的首例。该方法已用于制备多种环系，包括[3.2.1]-、[2.2.2]-和[2.2.1]-桥连碳双环化合物，以及稠合[5.5]环化合物。丙二酸根阴离子已被证明是这些共轭加成反应中有效的碳亲核试剂，简单酯的烯醇钾盐也已成功应用。
