The first asymmetric 1,4-addition of azlactones to α,β-unsaturated trichloromethyl ketones catalyzed by cinchona alkaloid derived bifunctional thiourea catalysts was developed. A series of α,α-disubstituted α-amino acid derivatives bearing a quaternary stereocenter at the α-position were obtained in high yields with excellent diastereo- and enantioselectivities (up to >20:1 dr and 99 % ee). In addition, the trichloromethyl moiety in these adducts was identified as a good leaving group.

Drug lead synthesis by the rapid construction of chiral molecular complexity around the biologically relevant framework using a highly efficient strategy is a key goal of organic synthesis. Herein, a highly efficient and convenient strategy that allows the rapid synthesis of highly optically active methylthioimidazolines through the novel rosin-derived thiourea-catalyzed asymmetric synthesis of cyclic thioureas with high levels of enantio- and diastereoselectivity (up to 99% ee, and 20:1 dr) via Mannich reaction is described fior the first time. Several of the new methylthioimidazolines showed extremely promising antipyretic activity in the development of neuroinflammation through preliminary biological studies. Additionally, to gain a better understanding of the structural stability-activity relationships, explicit molecular dynamics (MD) simulations in water at room temperature and at body temperature were investigated.

The doubly stereocontrolled organocatalytic aza-Henry reaction of nitroalkanes to N-Boc-imines generated in situ from a variety of substituted α-amido sulfones was investigated for the first time, in general, affording the corresponding products with high to excellent yields (up to 93% yield) and enantioselectivities (up to 98% ee), and satisfactory diastereoselectivies (anti/syn up to 98:2). Furthermore, these organocatalysts based on rosin have been proved to be the very effective promoters for this catalytic asymmetric process along side the Cinchona alkaloid-derived catalysts.

The first highly enantioselective phosphonylation of α,β-unsaturated N-acylpyrroles has been developed. Excellent yields (91–99 %) and enantioselectivities (up to >99 % enantiomeric excess (ee)) were observed for a broad spectrum of both phosphites and N-acylpyrroles under mild conditions. In particular, when diethyl phosphite was employed to test the scope of the N-acylpyrroles, almost optically pure products (98 to >99 % ee) were obtained for 20 examples of N-acylpyrroles. Moreover, optically pure α-substituted β- or γ-amino phosphonates can be obtained by several simple transformations of the pyrrolyl phosphonates. The versatility of the N-acylpyrrole moiety makes the phosphorus adducts powerful chiral building blocks that enable the synthesis of various phosphonate-containing compounds. Finally, the present strategy can also be applied to the asymmetric hydrophosphonylation of N-acylimines with high enantioselectivities (93 to >99 % ee).