6533b838fe1ef96bd12a4428
RESEARCH PRODUCT
Addition of dianions of carboxylic acids to imines. Influence of the acid in the outcome of the reaction
Salvador Gil GrauMargarita Parra AlvarezPablo Rodriguez Abadsubject
DiastereoselectivityDianions ; Imines ; Regioselectivity ; DiastereoselectivityDianionsRegioselectivityUNESCO::QUÍMICA:QUÍMICA::Química orgánica [UNESCO]IminesUNESCO::QUÍMICA::Química orgánica:QUÍMICA [UNESCO]description
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. Gil Grau, Salvador, Salvador.Gil@uv.es, Parra Alvarez, Margarita, Margarita.Parra@uv.es, Rodriguez Abad, Pablo, roapa@alumni.uv.es
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-01-01 |