A dual-catalysis/anion-binding approach to the kinetic resolution of allylic amines

Eric G Klauber; Nisha Mittal; Tejas K Shah; Daniel Seidel

doi:10.1021/ol200712b

A dual-catalysis/anion-binding approach to the kinetic resolution of allylic amines

Org Lett. 2011 May 6;13(9):2464-7. doi: 10.1021/ol200712b. Epub 2011 Apr 8.

Authors

Eric G Klauber¹, Nisha Mittal, Tejas K Shah, Daniel Seidel

Affiliation

¹ Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.

PMID: 21476518
DOI: 10.1021/ol200712b

Abstract

A dual-catalysis approach enables the small-molecule catalyzed kinetic resolution of allylic amines by acylation. By employing 2 mol % of each 4-(pyrrolidino)pyridine (PPY) and a readily available chiral hydrogen-bonding cocatalyst, the first nonenzymatic kinetic resolution of allylic amines was accomplished with s factors of up to 20.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Amines / chemistry*
Anions / chemistry
Catalysis
Kinetics
Molecular Structure
Stereoisomerism

Substances

Amines
Anions