Chen Ling, Minh Thi Le Thi, Bouillon Jean-Philippe, Poisson Thomas, Jubault Philippe
Normandie Univ., INSA Rouen UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France.
Institut Universitaire de France, 1 rue Descartes, 75231, Paris, France.
Chemistry. 2022 Jul 26;28(42):e202201254. doi: 10.1002/chem.202201254. Epub 2022 Jun 8.
The catalytic asymmetric synthesis of highly functionalized cyclopropanes from α-substituted allyl sulfones and silanes is reported. The reaction, using α-aryl diazoacetates or diacceptor diazo reagents, catalyzed by a chiral rhodium complex (Rh ((S)-BTPCP) ), furnished the corresponding cyclopropanes in moderate to high yields (27-97 %), high diastereoselectivities (68 : 32 to 20 : 1 d.r.) and moderate to excellent ee (40-99 %). This methodology offers a privileged access to an underexplored class of enantioenriched cyclopropanes with a high level of functionality, an asset for further post-functionalization and their incorporation into more complex structure.
报道了从α-取代烯丙基砜和硅烷催化不对称合成高度官能化环丙烷的方法。该反应使用α-芳基重氮乙酸酯或双受体重氮试剂，在手性铑配合物（Rh((S)-BTPCP)）催化下，以中等至高产率（27-97%）、高非对映选择性（68:32至20:1的非对映体比例）和中等至优异的对映体过量（40-99%）得到相应的环丙烷。该方法为获得一类功能丰富但研究较少的对映体富集环丙烷提供了一种特殊途径，这些环丙烷具有高水平的官能团，有利于进一步的后期官能化以及将它们纳入更复杂的结构中。
