Design and Synthesis of Planar Chiral Heterocyclic Carbene Precursors Derived from [2.2]Paracyclophane
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-bromo[2.2]paracyclophane was achieved with relatively high efficiency. Starting from (4S p,1...
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Veröffentlicht in: | Journal of organic chemistry 2008-06, Vol.73 (11), p.4330-4333 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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-bromo[2.2]paracyclophane was achieved with relatively high efficiency. Starting from (4S p,13R p)-4-amino-13-bromo[2.2]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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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo800468x |