40.1.1.3.3.6 Synthesis of Amines by Pericyclic Reactions Involving C=N Units (Update 2020)

W. Maison

Abstract

The synthesis of nitrogen heterocycles, such as piperidines and tetrahydroquinolines, with high chemo-, regio-, and stereoselectivity can be achieved via cycloaddition reactions that involve imine derivatives either as dienes or dienophiles. This topic was previously covered in Section 40.1.1.3.3, to which this chapter is an update, covering the literature from 2008 to 2019. The field has seen significant advances in recent years; this is particularly true for catalytic, enantioselective variants and new hetero-Diels–Alder variants using aza-o-quinone methides as reactive 1-azabutadienes. Both topics are therefore a special focus of this update.

Schlüsselwörter

aza-Diels–Alder reactions - imines - dienes - dienophiles - pericyclic reactions - piperidines - tetrahydroquinolines - [4 + 2] cycloaddition - Povarov reactions - Lewis acid catalysis - Brønsted acid catalysis - stereoselective synthesis

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