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C1-Symmetric Aminosulfoximines in Copper-Catalyzed Asymmetric Vinylogous Mukaiyama Aldol Reactions

โœ Scribed by Marcus Frings; Iuliana Atodiresei; Yutian Wang; Jan Runsink; Gerhard Raabe; Carsten Bolm

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
376 KB
Volume
16
Category
Article
ISSN
0947-6539

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โœฆ Synopsis

Abstract

Vinylogous Mukaiyamaโ€type aldol reactions have been catalyzed by a combination of Cu(OTf)~2~ and readily available C~1~โ€symmetric aminosulfoximines. After a fineโ€tuning of the reaction conditions and an optimization of the modularly assembled ligand structure, high stereoselectivities and excellent yields have been achieved in catalyzed reactions involving various electrophile/nucleophile combinations. The relative and absolute configurations of two products were assigned by Xโ€ray single crystal structure analysis and a comparison of calculated and experimental CD spectra.

๐Ÿ“œ SIMILAR VOLUMES

Highly Modular Synthesis of C1-Symmetric
Highly Modular Synthesis of C1-Symmetric Aminosulfoximines and Their Use as Ligands in Copper-Catalyzed Asymmetric Mukaiyama-Aldol Reactions
โœ Martin Langner; Pauline Rรฉmy; Carsten Bolm ๐Ÿ“‚ Article ๐Ÿ“… 2005 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 228 KB

## Abstract The development of __C__~1~โ€symmetric aminosulfoximines, their highly modular synthesis, and their application in enantioselective copperโ€catalyzed Mukaiyamaโ€type aldol reactions between pyruvates and enolsilanes is described. In this context, the influence of the ligand architecture as