The Diarylprolinol Silyl Ethers: Ten Years After

Abstract

Asymmetric organocatalysis has experienced an incredible development since the beginning of this century. The expansion of the field has led to a large number of efficient types of catalysts. One group, the diarylprolinol silyl ethers, was introduced in 2005 and has been established as one of the most frequently used in aminocatalysis. In this Minireview, we will take a look in the rear-view mirror, ten years after the introduction of the diarylprolinol silyl ethers. We will focus on the perspectives of the different activation modes made available by this catalytic system. Starting with a short introduction to aminocatalysis, we will outline the properties that have made the diarylprolinol silyl ethers a common choice of catalyst. Furthermore, we will describe the major tendencies in the activation and reaction concepts developed with regard to reactivity patterns and combinations with other activation concepts.

One-Pot Two-Step Organocatalytic Asymmetric Synthesis of Spirocyclic Piperidones via Wolff Rearrangement–Amidation–Michael–Hemiaminalization Sequence

“…Over the past decade, asymmetric organic catalysis [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17], quite powerful for synthesizing various heterocyclic molecules, has formed the basis of several elegant approaches to construct chiral single-heterocycle piperidine skeletons with high efficiency and low toxicity under environmentally friendly conditions . In contrast, relatively few organocatalytic methods have been described to stereo-selectively form spirocyclic piperidine derivatives [30][31][32][33][34][35][36], particularly ones with a quaternary stereocenter [37][38][39].…”

Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

“…Among the different structures usually found in organocatalysis, the five-membered secondary amine structure of pyrrolidine has proven to be a privileged motif [5] with a powerful capacity in aminocatalysis [6–10]. In this context diarylprolinol silyl ethers have proven to be extremely efficient organocatalysts for a wide variety of chemical transformations [11]. …”

Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams

“…Herein, we introduce a regio-, diastereo-, and enantioselective functionalization of γ-alkyl-β,γ-unsaturated γ-lactams utilizing α,β-unsaturated aldehydes as electrophiles and catalytic diphenylprolinol silyl ether (cat. I , Scheme 1), 11 as a highly effective means for accessing these privileged compounds.…”