Journal article
Metal-mediated dearomatization leading to 2-azaspiro[4.5]decanes via tandem nucleophilic aromatic addition–Horner–Wadsworth–Emmons olefination–oxidative demetalation sequences
Tetrahedron, Vol.64(44), pp.10123-10131
2008
DOI: 10.1016/j.tet.2008.08.024
Abstract
A ruthenium-mediated dearomatization sequence has been developed that delivers structurally intriguing azaspirolactam products in stereoselective fashion. Treatment of (η
6-arene)Ru(cyclopentadienyl) complexes bearing
N-benzyl-β-amido phosphonate side chains with excess NaH results in intramolecular nucleophilic aromatic addition to the
ipso position of the coordinated arenes. Subsequent Horner–Wadsworth–Emmons (HWE) reaction with added aldehydes affords olefinated spirolactam cyclohexadienyl ruthenium complexes. Mild oxidation with CuCl
2 or CuBr
2 under CO effects removal and recovery of the CpRu(II) fragment. Substituents present on the cyclohexadienyl skeleton influence the outcome of demetalation and products obtained in this study include functionalized 2-azaspiro[4.5]decanes and tetrahydroisoquinolinones.
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Details
- Title: Subtitle
- Metal-mediated dearomatization leading to 2-azaspiro[4.5]decanes via tandem nucleophilic aromatic addition–Horner–Wadsworth–Emmons olefination–oxidative demetalation sequences
- Creators
- F. Christopher PiggeRashmi Dalvi
- Resource Type
- Journal article
- Publication Details
- Tetrahedron, Vol.64(44), pp.10123-10131
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/j.tet.2008.08.024
- ISSN
- 0040-4020
- eISSN
- 1464-5416
- Language
- English
- Date published
- 2008
- Academic Unit
- Radiology; Chemistry
- Record Identifier
- 9984216697702771
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