.1. High-tert-butyl Grignard Reagent Derived From The Wood Of The D-furanose Imide Non-mapping Converged Addition Chiral Study On The Synthesis Of 2,2,3 - Trisubstituted Aziridines 3 Carbon Nanotubes Palladium-catalyzed Suzuki Coupling Reaction

Chiral t-butanesulfinyl is a versatile chiral auxiliary for the asymmetric synthesis of many importantα-branched chiral amines,however,its interplay with other chiral templates has not been investigated.Asymmetric synthesis of aziridines has been extensively studied,but no general method for the synthesis of 2,2,3-trisubstituted aziridines is available.Finally,interdisciplinary research concerning Suzuki coupling and nano-technology is a novel and interesting topic.This dissertation comprises the following parts:1.Unexpectedly high level of diastereoconvergence was observed in the addition of Grignard reagents to D-xylose-derived t-butanesulfinyl aldimines.The co-solvent for Grignard reagents was also critical.The effects of the protecting groups for the 3-hydroxyl and the C-3 configuration were estimated.The diastereoselectivity for vinyl Grignard addition to D-ribose-derived t-BS imines was as expected.2.Chiral vicinal diols obtained via Sharpless AD of trisubstituted olefins were converted to cyclic sulfites,opened by NaN₃,and underwent Staudinger reaction to afford trans-trisubstituted aziridines with inversion at both stereogenic centers. Alternatively,sequential mesylation of the secondary hydroxyl,epoxide formation, ring-opening by NaN₃,and Staudinger reaction afforded chiral aziridines with the complementary cis-stereochemistry.3.Pd-CNT efficiently catalyzed Suzuki-Miyaura coupling of arylbromides under ligandless and additive-free conditions in aqueous media.For hydrophilic substrates, the reaction could be carried out in neat water.The catalyst could be recycled and reused,meeting the criteria of green chemistry.