10.1021/jo00036a039
The research focuses on the synthesis of various chemical compounds and the exploration of a new class of enantioselective organoboron reducing agents. The purpose of the research was to develop and purify compounds such as 2,2-dinitropropyl vinyl ether (Product 6), 2,2,2-trinitroethyl vinyl ether (Compound 7), and 3-hydroxy-2,2-dinitropropyl vinyl ether (Compound 8) through a series of chemical reactions involving reagents like HgO, TFAA, CH2Cl2, neutral aluminum oxide, and H2O2. Additionally, the study aimed to investigate the enantioselective reductions of prochiral ketones using BH3 complexes of N-alkyl-10,10-dimethyl-5-aza-6-boratricyclo[7.1.1.02,7]undecanes, which demonstrated modest to high enantioselectivity. The chemicals used in these processes included borane complexes, nopylamines, and various ketones, among others. The conclusions drawn from the research highlighted the effectiveness of these new reducing agents in achieving enantioselective reductions and the importance of balancing the size of the groups on boron and nitrogen for an effective reagent. The study also provided a comparative analysis of charge-transfer excitation in aromatic electron donor-acceptor complexes with stannic chloride, offering insights into its behavior towards aromatic substrates.