Asymmetric Synthesis of Tetrahydropyridines via a Brønsted Acid Catalyzed Aza-Diels–Alder Reaction

Christian Beceño; Tim Krappitz; Gerhard Raabe; Dieter Enders

doi:10.1055/s-0034-1381058

Synthesis, Table of Contents

Synthesis 2015; 47(23): 3813-3821
DOI: 10.1055/s-0034-1381058

paper

Asymmetric Synthesis of Tetrahydropyridines via a Brønsted Acid Catalyzed Aza-Diels–Alder Reaction

Authors

Christian Beceño

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: enders@rwth-aachen.de
Tim Krappitz

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: enders@rwth-aachen.de
Gerhard Raabe

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: enders@rwth-aachen.de
Dieter Enders*

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: enders@rwth-aachen.de

Abstract

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Abstract

The asymmetric synthesis of tetrahydropyridines employing a normal electron-demanding aza-Diels–Alder reaction has been developed. The [4+2] cycloaddition of ethyl glyoxylate imine with aryl-substituted 2-silyloxy-1,3-butadienes is catalyzed by 5 mol% of a BINOL-derived phosphoric acid and in general leads to good yields and ee values with good to excellent diastereoselectivities. The cycloadducts can be further converted into the corresponding piperidinones, which are important pipecolic acid derivatives.

Key words

aza-Diels–Alder reaction - asymmetric synthesis - Brønsted acid - organocatalysis - glyoxylate imine

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Supplementary Material

Supporting Information (PDF)