ASYMMETRIC DECARBOXYLATIVE PROTONATION OF α

ASYMMETRIC DECARBOXYLATIVE PROTONATION OF α-AMINOMALONIC ESTERS FOR THE SYNTHESIS OF α-AMINO ACIDS Bradley L. Nilsson, University of Rochester, Department of Chemistry α-Amino acids (α-AAs) are among the most important and useful families of natural products. The objective of this PRF-funded research project has been to develop novel synthetic methods for the chemical synthesis of α-AAs that combine classical aminomalonate alkylation/decarboxylation with modern asymmetric catalysis. This work has been pursued in an effort to enable access to noncanical α-AAs that can be used in the creation of amyloid-inspired materials derived from α-AAs and peptides. Y

O

X

Z

O

O

O

R

O

O

N Ph

N H

OH O

PdLn* H+ source O O

R * N

Ph H+ +H N 3

* CO2H R

water

water