Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 4, Pages 1611-1620Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo802330x
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Funding
- Dreyfus Foundation
- Swarthmore College and HEMI
- Direct For Mathematical & Physical Scien [0742001] Funding Source: National Science Foundation
- Division Of Chemistry [0742001] Funding Source: National Science Foundation
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3-(2-Formylaryl)-1-sulfinyl-(1Z,3E)-pentadien-5-al iron tricarbonyl complexes were prepared to examine the feasibility and diastereoselectivity of intramolecular pinacol couplings on such substrates. It was found that the pinacol coupling, promoted by VCl(3)center dot(THF)(3)/Zn, proceeded in good yield and with high diastereoselectivity (>23:1 dr), provided the 2-formylaryl unit remained unsubstituted at the aryl C3 position (ortho to the formyl group). In these latter cases the pinacol coupling was diastereorandom. A 3-formyl-4-(2-formylaryl)-1-sulfinyl-(1Z,3E)-butadiene iron tricarbonyl complex also underwent diastereoselective pinacol coupling (22:1 dr). 3-(3-Formylindolyl)-1-sulfinyl-(1Z,3E)-pentadien-5-al iron tricarbonyl complexes were also prepared, though pinacol coupling of these substrates proceeded in, at best, modest yield for two of the four examples tested. All cases described herein represent the first intramolecular pinacol couplings performed on the periphery of an iron(0) diene tricarbonyl complex.
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