CHAPTER 11: Tetraenamine-catalyzed Stereoselective Cycloadditions of Polyunsaturated Carbonyl Compounds

Abstract

The recent progress in the ability of amine catalysis to functionalize polyunsaturated carbonyl compounds was made possible by highest occupied molecular orbital (HOMO)-raising or lowest unoccupied molecular orbital (LUMO)-lowering activations. In this context, the HOMO-raising dienamine and trienamine activation strategy has been explored extensively for the functionalization of polyconjugated carbonyl compounds at remote positions. This concept was recently stretched further to tetraenamine catalysis, a new activation strategy for amine-catalyzed HOMO-activation. The concept of tetraenamine catalysis is quite modern and only a few examples of the asymmetric Diels-Alder reaction are known so far. In this chapter, we will discuss the very first breakthroughs in the direction of tetraenamine catalysis.