Synthesis of Tetrahydropyrimidine-Based Acyl Transfer Catalysts and their Application to Enantioselective O- and C-Acylations
Date of Award
Doctor of Philosophy (PhD)
Structural variation of several types of amidine-based catalysts was explored, including variation of steric, electronic and other parameters. Enantioselective Steglich and related rearrangements were explored using HBTM-type catalysts previously developed in our group. Rearrangement of several oxazolyl carbonates revealed that phenoxycarbonyl migrating group is optimal. Rearrangement of benzofuran and oxindole enolcarbonates proceeded, but with only low enantioselectivity.
Chair and Committee
Vladimir B. Birman
Kevin Moeller, John-Stephen A. Taylor, John R. Bleeke, Garland R. Marshall, Donald L. Elbert
Padakanti, Prashanth K., "Synthesis of Tetrahydropyrimidine-Based Acyl Transfer Catalysts and their Application to Enantioselective O- and C-Acylations" (2010). Arts & Sciences Electronic Theses and Dissertations. 177.