Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 30, Pages 9939-9947Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201300844
Keywords
dibenzophospholes; enantioenriched helicenes; gold complexes; photocyclization; phosphahelicenes
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Funding
- ICSN
- Cost Action PhoSciNet [CM0802]
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The oxidative photocyclization reactions of olefins that contain 1H-phosphindole or dibenzophosphole substituents have been applied to the synthesis of P/N-bi-heterosubstituted dimeric helicenes, as well as of new [6]- and [8]phosphahelicenes. In these photocyclization processes, the configuration of the stereogenic phosphorus center dictates the sense of helical chirality. Thus, by starting from enantiomerically pure P-menthylphosphole-oxide units, this method affords enantiopure helical compounds. The helical phosphine oxides were characterized by X-ray diffraction. After reduction of the phosphine-oxides, the corresponding helical phosphines have been used as ligands in transition-metal complexes. The X-ray crystal structure of a gold chloride complex of a [6]helicene is reported.
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