DescriptionOrganocatalysis has played a role in the development of enantioselective catalytic
reactions, specifically pericyclic reactions, including cycloadditions and sigmatropic
rearrangements, especially in the past two decades. This dissertation presents a
comprehensive review and background on the development of new organocatalytic
pericyclic reactions methods, specifically cycloadditions and sigmatropic
rearrangements, leading to asymmetric small molecules. Herein, the research that
was conducted and lead to two successful new discoveries are described. The topics
specifically discussed in this dissertation are: 1.) Cycloaddition reactions catalyzed
by primary and secondary chiral amine catalysts since 2011. 2.) Sigmatropic
rearrangements that have been catalyzed by organocatalysts in general. 3.) A novel
[5 + 2] cycloaddition reaction catalyzed by a diphenyl prolinol silyl ether. 4.) A
Claisen rearrangement kinetic resolution of g-substituted O-allyl a,b-unsaturated
aldehydes catalyzed by 2,5-diphenyl pyrrolidine. The methodologies reviewed are
all groundbreaking achievements improving the scope of pericyclic reactions that
achieve optically active products, that can potentially act as precursors to even larger
chiral building blocks as a part of molecular architectures.