Start of funding 01.07.2010

Palladium Catalyzed Asymmetric Allylic Alkylations of N-Heterocycles

Prof. Dr. Timothy Clark
Friedrich-Alexander-University of Erlangen-Nuremberg
Computer Chemistry Center (CCC)

Prof. Dr. Barry M. Trost
Stanford University
Department of Chemistry



Asymmetric molecules are an important and in some cases difficult challenge in chemistry. Palladium-catalyzed asymmetric allylic alkylations (Pd-AAA) can be a very powerful tool for optimizing the synthesis of or even obtain access to certain asymmetric moieties.

Chiral ligands have previously been used to create chiral space around a metal centre to allow selective reactions to occur. The primary goal of this research project is to develop a general method using nitrogen heterocycles as nucleophiles and allylic electrophiles in palladium catalyzed asymmetric allylic alkylations (pd-AAA). The known scope of N-nucleophiles and electrophiles will be extended and the ligands will be screened for optimal selectivity. Computational studies will be used to help achieve Pd-AAA reactions in the desired manner.

A new pd-AAA reaction is proposed, which can be used to obtain rapid access to biologically active compounds, like agelestatin a, ribavirin, levovirin, and carbovir.