Aminocatalysis: A Computational Study

Abstract

Small organic molecules containing an amine functional group have been shown to catalyze a wide range of important organic transformations of carbonyl compounds, e.g. the aldol reaction, the Michael addition and the SOMO (Singly Occupied Molecular Orbital) reaction, generally with good to excellent stereoselectivities. While tremendous progress has been made in the development of novel aminocatalysts in the last decade, the corresponding understanding of the reaction mechanism through studying reactive intermediates and transition structures is somehow limited. In the first part of this talk, we apply a computational approach to investigate the catalytic mechanism and the origin of stereoselectivity of an allylation reaction of aldehyde, which employs the recently discovered SOMO activation mode. In the second part, we report our efforts to design ?in silico? an aminocatalyst for the Michael reaction of aldehyde.