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.C
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 %.
Pub Type(s)
Journal Article
Language
eng
PubMed ID
16075444
Citation
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, no. 21, 2005, pp. 6254-65.
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):6254-65.
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.
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. PubMed PMID: 16075444.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions.
AU - Langner,Martin,
AU - Rémy,Pauline,
AU - Bolm,Carsten,
PY - 2005/8/3/pubmed
PY - 2005/8/3/medline
PY - 2005/8/3/entrez
SP - 6254
EP - 65
JF - Chemistry (Weinheim an der Bergstrasse, Germany)
JO - Chemistry
VL - 11
IS - 21
N2 - 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 %.
SN - 0947-6539
UR - https://www.unboundmedicine.com/medline/citation/16075444/Highly_modular_synthesis_of_C1_symmetric_aminosulfoximines_and_their_use_as_ligands_in_copper_catalyzed_asymmetric_Mukaiyama_aldol_reactions_
DB - PRIME
DP - Unbound Medicine
ER -
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