DEVELOPING ENANTIOSELECTIVE CYCLOADDITIONS OF REDOX-ACTIVE-DERIVED REAGENTS: A LATENT STRATEGY TO ESTABLISH MOLECULAR COMPLEXITY

The past several decades have witnessed the development of tremendous amounts of organo-catalyzed enantioselective construction of chiral cyclic compounds. Notably, the chiral Lewis-acid-catalyzed Diels-Alder reaction was proved to be an efficient method to establish multi-substituted 6-membered ring system; and the asymmetric Lu’s [3+2] annulation provides an essential strategy to construct chiral 5-membered cyclopentene derivatives. Despite these appealing abilities, many of these asymmetric catalytic reactions developed previously are less used in practical synthesis of natural products or bioactive candidates, limited by the lack of modularity and the overreliance of specific substrates and catalysts. In this thesis, we developed several expeditious accesses to miscellaneous chiral multi-substituted ring systems, utilizing reagents incorporating an N-hydroxyphthalimide ester moiety as a "latent functional group." This innovative design has paved the way for the development of new procedures for installing various functional groups, thereby establishing C(sp3)-complexity. Moreover, these methods represent a departure from traditional synthetic logic and offer promising avenues for enhancing the practical utility of asymmetric catalytic reactions in the synthesis of complex molecules.

Author dc:creator

• SHEN ZIAN

• Lewis-acid
• Asymmetric-catalysis
• Norbornane
• Phosphine
• Redox-active-esters
• Cycloaddition