Journal article
Exploiting Phosphonate Chemistry in Metal-Mediated Dearomatization: Stereoselective Construction of Functionalized Spirolactams from Arene Ruthenium Complexes
Journal of the American Chemical Society, Vol.128(11), pp.3498-3499
03/22/2006
DOI: 10.1021/ja058342y
PMID: 16536505
Abstract
Arene ruthenium complexes possessing β-amido phosphonate side chains participate in intramolecular spirocyclization reactions to deliver stable cyclohexadienyl ruthenium adducts. Spirocyclization is accomplished via a tandem two-step sequence that involves stereoselective nucleophilic aromatic addition to the ipso position of the coordinated arene, followed by intermolecular Horner−Wadsworth−Emmons olefination. The resulting η5-cyclohexadienyl complexes can then be diastereoselectively converted to metal-free azaspiro[4.5]decane derivatives upon oxidative demetalation in the presence of suitable nucleophiles. An asymmetric spirocyclization was demonstrated through application of this procedure to a β-amido phosphonate prepared from (S)-(−)-α-methyl benzylamine. The expected spirolactam product was obtained as a single enantiomer.
Details
- Title: Subtitle
- Exploiting Phosphonate Chemistry in Metal-Mediated Dearomatization: Stereoselective Construction of Functionalized Spirolactams from Arene Ruthenium Complexes
- Creators
- F. Christopher PiggeJohn J ConiglioRashmi Dalvi
- Resource Type
- Journal article
- Publication Details
- Journal of the American Chemical Society, Vol.128(11), pp.3498-3499
- Publisher
- American Chemical Society
- DOI
- 10.1021/ja058342y
- PMID
- 16536505
- ISSN
- 0002-7863
- eISSN
- 1520-5126
- Language
- English
- Date published
- 03/22/2006
- Academic Unit
- Radiology; Chemistry
- Record Identifier
- 9984216699602771
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