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Langner M, Rémy P, Bolm C. Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions. Chemistry. 2005;11(21):6254-65doi: 10.1002/chem.200500497.
Langner, M., Rémy, P., & Bolm, C. (2005). Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions. Chemistry (Weinheim an der Bergstrasse, Germany), 11(21), 6254-65. https://doi.org/10.1002/chem.200500497
Langner, Martin, et al. "Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 11,21 (2005): 6254-65. doi: https://doi.org/10.1002/chem.200500497
Langner M, Rémy P, Bolm C. Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions. Chemistry. 2005 Oct 21;11(21):6254-65. doi: 10.1002/chem.200500497. PMID: 16075444.
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Chemistry. 2005 Oct 21;11(21):6254-65. doi: 10.1002/chem.200500497.

Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Martin Langner, Pauline Rémy, Carsten Bolm

Affiliations

  1. Institut für Organische Chemie der Rheinisch-Westfälischen Technischen Hochschule Aachen, Germany.

PMID: 16075444 DOI: 10.1002/chem.200500497

Abstract

The development of C1-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 %.

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