Hierarchically assembled helicates as reaction platform – From stoichiometric Diels-Alder reactions to enamine catalysis

Abstract

The stereoselectivity of a Diels-Alder reaction within the periphery of hierarchically assembled titanium(IV) helicates formed from mixtures of achiral, reactive and chiral, unreactive ligands is investigated in detail. Following the pathway of the chiral induction, the chiral ligands, solvents as well as substituents at the dienophile are carefully varied. Based on the results of the stoichiometric reaction a secondary amine catalyzed nitro-Michael reaction is performed as well which affords reasonable diastereoselectivities.

Authors 7

1. David Van Craen Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry , RWTH Aachen University , Landoltweg 1 , 52074 Aachen , Germany

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

2. Jenny Begall Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry , RWTH Aachen University , Landoltweg 1 , 52074 Aachen , Germany

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

3. Johannes Großkurth Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry , RWTH Aachen University , Landoltweg 1 , 52074 Aachen , Germany

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

4. Leonard Himmel Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry , RWTH Aachen University , Landoltweg 1 , 52074 Aachen , Germany

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

5. Oliver Linnenberg Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry , RWTH Aachen University , Landoltweg 1 , 52074 Aachen , Germany

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

6. Elisabeth Isaak Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry , RWTH Aachen University , Landoltweg 1 , 52074 Aachen , Germany

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

7. Markus Albrecht corresponding Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry , RWTH Aachen University , Landoltweg 1 , 52074 Aachen , Germany

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany