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Stereoselective Mannich-type reaction of chlorotitanium α-phenylseleno esters enolates with aromatic aldimines |
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| Authors: | Claudio C. Silveira Adriano S. Vieira Dennis Russowsky |
| Affiliation: | a Departamento de Química, Universidade Federal de Santa Maria, UFSM, C.P. 5001, 97105-900 Santa Maria, RS, Brazil b Instituto de Química, Universidade Federal do Rio Grande do Sul, 91501-970 Porto Alegre, RS, Brazil |
| Abstract: | The stereoselective Mannich-type reaction of α-phenylseleno chlorotitanium enolates with aromatic aldimines is described. The corresponding α-phenylseleno-β-amino esters were obtained in good yields and with moderate to good diastereoselectivity. A rationale for the predominant syn selectivity based on a chelated cyclic transition state is suggested. The obtained compounds are useful synthetic tools and direct precursors of new α-phenylseleno-β-lactams. |
| Keywords: | Mannich reaction Phenylseleno esters α-Seleno-β-amino esters Stereoselective |
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