Synthesis of Tetrahydropyrimidine-Based Acyl Transfer Catalysts and their Application to Enantioselective O- and C-Acylations

Author

Prashanth K. Padakanti, Washington University in St. LouisFollow

Date of Award

Spring 5-15-2010

Author's School

Graduate School of Arts and Sciences

Author's Department

Chemistry

Degree Name

Doctor of Philosophy (PhD)

Degree Type

Dissertation

Abstract

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.

Language

English (en)

Chair and Committee

Vladimir B. Birman

Committee Members

Kevin Moeller, John-Stephen A. Taylor, John R. Bleeke, Garland R. Marshall, Donald L. Elbert

Comments

Permanent URL: https://doi.org/10.7936/K72V2D1N

Recommended Citation

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.
https://openscholarship.wustl.edu/art_sci_etds/177