Applications of partially fluorinated binaphthol ligands in asymmetric catalysis and synthesis of alpha-amino acid derivatives.
Contributors: University of Toronto.  Dept. of Chemistry.
Published: 2005
Language: eng
Number of pages: 220
Description: This thesis is divided into two parts: synthesis, understanding and application of partially fluorinated binaphthols in asymmetric catalysis and catalytic asymmetric synthesis of alpha-amino acid derivatives.Chapter 1 describes the synthesis of F8BINOL, synthesis of F4BINOL and nucleophilic aromatic substitution of fluorine on protected F8BINOL by heteroatom nucleophiles. Chapter 2 discusses application of the fluorinated binaphthyl ligands in the titanium-catalyzed asymmetric diethylzinc addition, Friedel-Crafts reaction, and in the asymmetric epoxidation of trans-alpha,beta-unsaturated ketones catalyzed by the lanthanoid complexes. Comparison of both reactivity and stereoselectivity of the fluorinated binaphthyl compounds to other commercially available and commonly used derivatives within the BINOL family is also included.Chapter 3 focuses on asymmetric synthesis of alpha-amino acid derivatives, including the first synthesis of aspartic acid derivatives from glycine precursors through palladium catalyzed aza-allylic alkylation reaction and study of the synthesis of alpha-fluorinated amino acids from benzophenone-based imines of glycine alkyl esters as model substrates.
Notes: Advisor: Andrei Yudin

Thesis (Ph.D.)--University of Toronto, 2005.

Electronic version licensed for access by U. of T. users.

Source: Dissertation Abstracts International, Volume: 66-06, Section: B, page: 3133.