10.1039/c2ob25709b
The research focuses on the one-pot synthesis of 2-aminoquinoline-based alkaloids, which are significant in pharmaceuticals due to their anthelmintic, antiprotozoal, antidepressant, and antihypertensive properties, as well as their potential role in Alzheimer's disease therapeutics. The study utilizes α-diaminoboryl carbanions, derived from acetonitrile, to stereoselectively convert 2-nitrobenzaldehydes into nitrophenyl (Z)-acrylonitriles, which then undergo reductive cyclization to form a series of 2-aminoquinoline derivatives. The experiments involve the use of various reagents, including nBuLi, (i-Pr2N)2BCl, and zinc powder, and are conducted under controlled conditions with specific attention to temperature and reaction times. The success of the synthesis is determined through techniques like column chromatography and spectroscopic analyses, including 1H and 13C NMR, as well as HRMS, to confirm the structure and purity of the synthesized compounds.
10.1016/j.tetasy.2004.08.009
The study focuses on the synthesis and application of chiral amino thiols as catalysts in the enantioselective addition of diethylzinc to aldehydes, starting from (S)-(-)-valine. A series of new chiral amino thiol and corresponding thioacetate ligands were prepared and utilized in the asymmetric addition, demonstrating excellent enantioselectivity of up to 99% ee with a remarkably low catalyst loading of 0.02mol%. The study highlights the superior performance of these chiral amino thiols compared to traditional amino alcohols, attributing this to the softness of sulfur which exhibits a greater affinity to zinc, in line with the hard soft acid base (HSAB) principle. The research also explores the effect of reaction temperature and solvent on enantioselectivity, finding that less polar solvents without coordinating atoms are more favorable for achieving high ee values. The results underscore the potential of these chiral ligands in asymmetric catalysis, offering a highly efficient and stereoselective method for the addition of diethylzinc to aldehydes.
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