Stereoselective synthesis of carane-based chiral β- And γ-amino acid derivatives via conjugate addition
Michael addition of dibenzylamine to (-)-tert-butyl isochaminate, prepared in three steps from (-)-perillaldehyde, furnished a carane-based β-amino acid derivative in a highly stereospecific reaction. The resulting amino ester was transformed to the bicyclic amino acid, a promising building block fo...
Elmentve itt :
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| Dokumentumtípus: | Cikk |
| Megjelent: |
2015
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| Sorozat: | TETRAHEDRON
71 No. 29 |
| doi: | 10.1016/j.tet.2015.05.019 |
| mtmt: | 2922865 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/6007 |
| Tartalmi kivonat: | Michael addition of dibenzylamine to (-)-tert-butyl isochaminate, prepared in three steps from (-)-perillaldehyde, furnished a carane-based β-amino acid derivative in a highly stereospecific reaction. The resulting amino ester was transformed to the bicyclic amino acid, a promising building block for the synthesis of 1,3-heterocycles and peptidomimetics. The conjugate addition of nitromethane to α,β-unsaturated methyl ester likewise resulted in nitro esters in stereospecific reactions. Catalytic reduction of the nitro group yielded a γ-amino ester. Under acidic conditions, the hydrolysis of the methyl ester resulted in an unexpected aminolactone-type product through rearrangement of the bicyclic carane system, whereas an alternative synthetic pathway through α,β-unsaturated benzyl ester furnished the desired γ-amino acid. © 2015 Elsevier Ltd. All rights reserved. |
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| Terjedelem/Fizikai jellemzők: | 4846-4852 |
| ISSN: | 0040-4020 |