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

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.

Committee Chair

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

Degree

Doctor of Philosophy (PhD)

Author's Department

Chemistry

Author's School

Graduate School of Arts and Sciences

Document Type

Dissertation

Date of Award

Spring 5-15-2010

Language

English (en)

DOI

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 Theses and Dissertations. 177.

The definitive version is available at https://doi.org/10.7936/K72V2D1N