The first total synthesis of (R)-Convolutamydine A has been achieved by the organocatalytic addition of acetone to 4,6-dibromoisatin. The absolute configuration was determined by single crystal X-ray diffraction. DFT studies were used to model the transition states for the aldol reaction and equilibrium geometries of the post-aldol reaction intermediates. The DFT study revealed that the aldol bond forming reaction was considerably endothermic.
G. Luppi, M. Monari, R. J. Corrêa, F. de A. Violante, A. C. Pinto, B. Kaptein, et al. (2006). The First Total Synthesis of (R)-Convolutamydine A. TETRAHEDRON, 62, 12017-12024 [10.1016/j.tet.2006.09.077].
The First Total Synthesis of (R)-Convolutamydine A
LUPPI, GIANLUIGI;MONARI, MAGDA;TOMASINI, CLAUDIA
2006
Abstract
The first total synthesis of (R)-Convolutamydine A has been achieved by the organocatalytic addition of acetone to 4,6-dibromoisatin. The absolute configuration was determined by single crystal X-ray diffraction. DFT studies were used to model the transition states for the aldol reaction and equilibrium geometries of the post-aldol reaction intermediates. The DFT study revealed that the aldol bond forming reaction was considerably endothermic.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
