Aza-Conjugate Addition Methodology for the Synthesis of N-Hydroxy-isoindolin-1-ones

Santiago Royo; Robert S L Chapman; Alisia M Sim; Lucy R Peacock; Steven D Bull

doi:10.1021/acs.orglett.6b00261

Aza-Conjugate Addition Methodology for the Synthesis of N-Hydroxy-isoindolin-1-ones

Org Lett. 2016 Mar 4;18(5):1146-9. doi: 10.1021/acs.orglett.6b00261. Epub 2016 Feb 22.

Authors

Santiago Royo¹, Robert S L Chapman², Alisia M Sim², Lucy R Peacock², Steven D Bull²

Affiliations

¹ Departament de Química Inorgànica i Orgànica, Universitat Jaume I , Castelló, Spain.
² Department of Chemistry, University of Bath , Bath, BA2 7AY, U.K.

PMID: 26900784
DOI: 10.1021/acs.orglett.6b00261

Abstract

Aryl-aldehydes containing ortho-substituted propiolate fragments react with hydroxylamine to afford carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford N-hydroxy-2.3-dihydro-isoindolin-1-ones that can be reduced to their corresponding isoindolin-1-ones and isoindoles.

Publication types

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