Catalytic synthesis of azeheterocycles from organic azides.
One electron oxidation of bicyclic cyclopropanol, bicyclo[4.1.0]heptan-1-ol by a catalytic amount of Mn(III) promotes ring-expansion to afford 7-membered-ring β-carbonyl radical, which adds to vinyl azide to form an iminyl radical with elimination of dinitrogen. Iminyl radical then cyclizes with a...
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| Format: | Final Year Project |
| Language: | English |
| Published: |
2010
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| Online Access: | http://hdl.handle.net/10356/38933 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | One electron oxidation of bicyclic cyclopropanol, bicyclo[4.1.0]heptan-1-ol by a catalytic amount of Mn(III) promotes ring-expansion to afford 7-membered-ring β-carbonyl radical, which adds to vinyl azide to form an iminyl radical with elimination of dinitrogen. Iminyl radical then cyclizes with an intramolecular carbonyl moiety to give an iminyl radical addition product, 8-phenyl-7-azabicyclo[4.3.1]dec-7-en-6-ol. Upon one-pot treatment with sodium cyanoborohydride, C-O bond reduction occurs first giving 8-phenyl-7-azabicyclo[4.3.1]dec-7-ene, followed by C=N bond reduction giving 8-phenyl-7-azabicyclo[4.3.1]decane in high yield and diasteroselectivity. |
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