A Novel Concept in Combinatorial Chemistry in Solution with the Advantages of Solid-Phase Synthesis: Formation of N-Betaines by Multicomponent Domino Reactions

Lutz F Tietze; Holger Evers; Enno Töpken

doi:10.1002/1521-3773(20010302)40:5<903::AID-ANIE903>3.0.CO;2-7

A Novel Concept in Combinatorial Chemistry in Solution with the Advantages of Solid-Phase Synthesis: Formation of N-Betaines by Multicomponent Domino Reactions

Angew Chem Int Ed Engl. 2001 Mar 2;40(5):903-905. doi: 10.1002/1521-3773(20010302)40:5<903::AID-ANIE903>3.0.CO;2-7.

Authors

Lutz F Tietze¹, Holger Evers¹, Enno Töpken¹

Affiliation

¹ Institut für Organische Chemie der Universität Tammannstrasse 2, 37077 Göttingen (Germany) Fax: (+49) 551-39-9476.

PMID: 29712158
DOI: 10.1002/1521-3773(20010302)40:5<903::AID-ANIE903>3.0.CO;2-7

Abstract

Advantages of solid-phase and liquid-phase synthesis are combined in a new concept of combinatorial chemistry: a domino sequence comprising Knoevenagel and hetero-Diels-Alder reactions with subsequent hydrogenation starting from protected aminoaldehydes, 1,3-dicarbonyl compounds, and enol ethers leads to N-heterocycles of high diversity with a betaine structure, which are isolated in highly pure form by precipitation with diethyl ether. Cbz=benzyloxycarbonyl, Bn=benzyl.

Keywords: amino aldehydes; betaines; combinatorial chemistry; domino reactions; multicomponent reactions.