Evidence for the non-concerted 4+2 -cycloaddition of N-aryl imines when acting as both dienophiles and dienes under Lewis acid-catalysed conditions

Hermitage, S.; Jay, D.A.; Whiting, A.

Abstract

The ytterbium(III) triflate-catalysed reaction of a para-methoxyaniline, ethyl glyoxalate-derived imine, with a series of different dienes has resulted in products which initially suggest the operation of two possible modes of aza-Diels-Alder reaction, however, a more likely explanation is that a common reaction mechanism is operating, involving a stepwise Lewis acid-catalysed process and a common type of zwitterionic ytterbium complex. (C) 2002 Elsevier Science Ltd. All rights reserved.

Citation

Hermitage, S., Jay, D., & Whiting, A. (2002). Evidence for the non-concerted 4+2 -cycloaddition of N-aryl imines when acting as both dienophiles and dienes under Lewis acid-catalysed conditions. Tetrahedron Letters, 43(52), 9633-9636

• Journal Article Type: Article
• Publication Date: 2002-12
• Journal: Tetrahedron Letters
• Print ISSN: 0040-4039
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 43
• Issue: 52
• Pages: 9633-9636