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Addition of dianions of carboxylic acids to imines. Influence of the acid in the outcome of the reaction
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Addition of dianions of carboxylic acids to imines. Influence of the acid in the outcome of the reaction
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| Gil Grau, Salvador; Parra Alvarez, Margarita; Rodriguez Abad, Pablo | |||
| Aquest document és un/a article, creat/da en: 2009 | |||
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Este documento está disponible también en : http://www.arkat-usa.org/get-file/29567/ |
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| The addition of different carboxylic acids dianions to N-benzylidenebenzeneamine have been studied. The outcome of the reaction depends on the acid. Saturated ones lead to β-aminoacids with good yields and syn-selectivity whereas α,β-unsaturated ones lead to α− and γ− regioisomers with a regioselectivity that depends on the steric hindrance around the reactive centre. From some of these unsaturated acids, polyunsaturated carboxylic acids can be obtained as a change in the reaction conditions lead to the in situ elimination of aniline. From o-methyl aromatic acids δ-aminoacids are isolated with uneven results. Those derived from six member arene carboxylic acids give, on standing, dihydro-2-pyridones as the sole product. | |||
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