Syntheses of Enantiopure Bifunctional 2‑Guanidinobenzimidazole Cyclopentadienyl Ruthenium Complexes: Highly Enantioselective Organometallic Hydrogen Bond Donor Catalysts for Carbon–Carbon Bond Forming Reactions
2-Guanidinobenzimidazole (GBI) derivatives with a NHR group in place of NH2 (R: a, CH2Ph; b, (S C)-CH(CH3)Ph; c, (R C R C)-CH(CH2)4CHNMe2; d, (R C R C)-CH(CH2)4CH-NCH2(CH2)3 CH2) are prepared in four steps from 2-aminobenzimidazole. Reactions with [(η5-C5H5)Ru(CO)(NCCH3)2]+PF6 – (5 +PF6 –) af...
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| Veröffentlicht in: | Organometallics 2014-12, Vol.33 (23), p.6723-6737 |
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| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | 2-Guanidinobenzimidazole (GBI) derivatives with a NHR group in place of NH2 (R: a, CH2Ph; b, (S C)-CH(CH3)Ph; c, (R C R C)-CH(CH2)4CHNMe2; d, (R C R C)-CH(CH2)4CH-NCH2(CH2)3 CH2) are prepared in four steps from 2-aminobenzimidazole. Reactions with [(η5-C5H5)Ru(CO)(NCCH3)2]+PF6 – (5 +PF6 –) afford the chiral-at-metal chelates [(η5-C5H5)Ru(CO)(GBI-R)]+ PF6 – (6a–d +PF6 –, 39–77%), which have been characterized by NMR (1H, 13C, 31P, 19F) and other spectroscopy. The Ru,C configurational diastereomers of the dimethylamino containing complex 6c +PF6 – separate upon alumina chromatography (R Ru R C R C, >99:01 dr; S Ru R C R C, |
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| ISSN: | 0276-7333 1520-6041 |
| DOI: | 10.1021/om500705s |