Realizing an Aza Paternò-Büchi Reaction

Elango Kumarasamy; Sunil Kumar Kandappa; Ramya Raghunathan; Steffen Jockusch; Jayaraman Sivaguru

doi:10.1002/anie.201702273

Realizing an Aza Paternò-Büchi Reaction

Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7056-7061. doi: 10.1002/anie.201702273. Epub 2017 Apr 28.

Authors

Elango Kumarasamy¹, Sunil Kumar Kandappa¹, Ramya Raghunathan¹, Steffen Jockusch², Jayaraman Sivaguru¹

Affiliations

¹ Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, 58108, USA.
² Department of Chemistry, Columbia University, New York, NY, 10027, USA.

PMID: 28452104
DOI: 10.1002/anie.201702273

Abstract

Intramolecular atropselective aza Paternò-Büchi reaction involving atropisomeric enamide and imine functionalities under sensitized irradiation leads to azetidine products in good yield and selectivity (ee >96 %). A mechanistic model based on detailed photophysical and isomerization kinetic studies is provided that shed light into the reactivity of enamides leading to aza Paternò-Büchi reaction.

Keywords: [2+2]-photocycloaddition; asymmetric photoreaction; atropselectivity; aza Paternò-Büchi reaction; imines.

Publication types

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