𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Highly Modular Synthesis of C1-Symmetric Aminosulfoximines and Their Use as Ligands in Copper-Catalyzed Asymmetric Mukaiyama-Aldol Reactions

✍ Scribed by Martin Langner; Pauline Rémy; Carsten Bolm

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
228 KB
Volume
11
Category
Article
ISSN
0947-6539

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The development of C~1~‐symmetric aminosulfoximines, their highly modular synthesis, and their application in enantioselective copper‐catalyzed Mukaiyama‐type aldol reactions between pyruvates and enolsilanes is described. In this context, the influence of the ligand architecture as well as the optimization of the reaction conditions are discussed. In detail, the dependence of the catalyst efficiency on the solvent, the metal source and the temperature are reported, and an interesting additive effect is highlighted. Furthermore, the substrate scope will be presented. With the optimized catalyst system, a number of aldol products with quaternary stereogenic centers have been obtained in high yields and with enantiomeric excesses up to 99 %.

📜 SIMILAR VOLUMES

C1-Symmetric Aminosulfoximines in Copper
C1-Symmetric Aminosulfoximines in Copper-Catalyzed Asymmetric Vinylogous Mukaiyama Aldol Reactions
✍ Marcus Frings; Iuliana Atodiresei; Yutian Wang; Jan Runsink; Gerhard Raabe; Cars 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 376 KB 👁 1 views

## Abstract Vinylogous Mukaiyama‐type aldol reactions have been catalyzed by a combination of Cu(OTf)~2~ and readily available __C__~1~‐symmetric aminosulfoximines. After a fine‐tuning of the reaction conditions and an optimization of the modularly assembled ligand structure, high stereoselectiviti