The synthesis of 6-methyl perihydropyrimidin-4-ones (1′S,6R)-3a and (1′S,6S)-3b is reported starting from rac-3-aminobutanoic acid. The aldol condensation of various metal enolates of 3a and 3b with benzaldehyde and acetaldehyde is reported. All reactions afford complete facial diastereoselectivity and good simple diastereoselectivity, depending on the nature of the enolate and of the aldehyde. The reaction yields are generally good and the aldols have been characterized by means of 1H NMR spectroscopy and NOEDIFF experiments. © 1993.
Amoroso R., Cardillo G., Mobbili G., Tomasini C. (1993). Metal-assisted aldol condensation of chiral 6-methyl perihydropyrimidin-4-ones. TETRAHEDRON-ASYMMETRY, 4(10), 2241-2254 [10.1016/S0957-4166(00)80074-9].
Metal-assisted aldol condensation of chiral 6-methyl perihydropyrimidin-4-ones
Tomasini C.
1993
Abstract
The synthesis of 6-methyl perihydropyrimidin-4-ones (1′S,6R)-3a and (1′S,6S)-3b is reported starting from rac-3-aminobutanoic acid. The aldol condensation of various metal enolates of 3a and 3b with benzaldehyde and acetaldehyde is reported. All reactions afford complete facial diastereoselectivity and good simple diastereoselectivity, depending on the nature of the enolate and of the aldehyde. The reaction yields are generally good and the aldols have been characterized by means of 1H NMR spectroscopy and NOEDIFF experiments. © 1993.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
