Design and synthesis of planar chiral heterocyclic carbene precursors derived from [2.2]paracyclophane |
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Authors: | Duan Wenzeng Ma Yudao Xia Houqi Liu Xueying Ma Qingshuang Sun Junshan |
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Institution: | Department of Chemistry, Shandong University, Shanda South Road No. 27, Jinan, People's Republic of China. |
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Abstract: | A unique family of planar chiral symmetrical N-heterocyclic carbene precursors with restricted flexibility derived from 2.2]paracyclopane were obtained by a new synthetic route. The resolution of 4-amino-13-bromo2.2]paracyclophane was achieved with relatively high efficiency. Starting from (4 S p,13 R p)-4-amino-13-bromo2.2]paracyclophane, the planar chiral pseudogem-disubstituted 2.2]paracyclophanyl dihydroimidazoliums were prepared in a four-step sequence with good yields. The resulting dihydroimidazolium salts were fully characterized with a series of methods including single-crystal X-ray diffraction technique. |
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