Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 46, Pages 16678-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9079308
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- National Institutes of Health [CA 22215]
- Eisai Research Institute
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Two new ligands 1a,b are reported. Upon treatment with 1 equiv of NiCl2 center dot(MeOCH2)(2), 1a,b give the corresponding Ni complexes. X-ray analysis of 1a-NiCl2 established that the NiCl2 is selectively coordinated to the phenanthroline nitrogens. Ni/Cr heterobimetallic catalysts 1a,b center dot CrCl2/NiCl2, prepared from 1a,b center dot NiCl2, have been shown to behave exceptionally well in catalytic asymmetric Ni/Cr-mediated couplings, with highlights including the following: (1) 1-2 mol % catalyst is sufficient to complete the coupling; (2) only negligible amounts of the dimers, byproducts formed through the alkenyl Ni species, are observed; (3) the coupling goes to completion even with a 1:1 molar ratio of the coupling partners; and (4) the asymmetric induction is practically identical with that obtained from the coupling with the Cr catalysts prepared from (S)-sulfonamides 2a,b. The scope of the new Ni/Cr heterobimetallic catalysts was briefly studied using four additional aldehydes. The applicability of the new catalysts to polyfunctional substrates was demonstrated by two C-C bond formations chosen from the hatichondrin/E7389 synthesis as examples.
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