Revisited Mechanistic Implications of the Joullié-Ugi Three-Component Reaction

Akira Katsuyama; Akira Matsuda; Satoshi Ichikawa

doi:10.1021/acs.orglett.6b00827

Revisited Mechanistic Implications of the Joullié-Ugi Three-Component Reaction

Org Lett. 2016 Jun 3;18(11):2552-5. doi: 10.1021/acs.orglett.6b00827. Epub 2016 May 23.

Authors

Akira Katsuyama¹, Akira Matsuda^{1

2}, Satoshi Ichikawa^{1

2}

Affiliations

¹ Faculty of Pharmaceutical Sciences, Hokkaido University , Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
² Center for Research and Education on Drug Discovery, Faculty of Pharmaceutical Sciences, Hokkaido University , Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

PMID: 27210481
DOI: 10.1021/acs.orglett.6b00827

Abstract

The effect of the solvent on the diastereoselectivity of the Joullié-Ugi three-component reaction (JU-3CR) using an α-substituted five-membered cyclic imine is revisited. The cis and trans isomers were generated in toluene and HFIP, respectively. Hammett analysis of the JU-3CR suggests the presence of two reaction mechanisms.

Publication types

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