121411-07-2Relevant academic research and scientific papers
Asymmetric, Nearly Barrierless C(sp3)-H Activation Promoted by Easily-Accessible N-Protected Aminosulfoxides as New Chiral Ligands
Jerhaoui, Soufyan,Djukic, Jean-Pierre,Wencel-Delord, Joanna,Colobert, Fran?oise
, p. 2532 - 2542 (2019/03/07)
Although chiral sulfoxides are important motifs in medicinal chemistry and asymmetric synthesis, design and applications of sulfoxide ligands are still limited, in particular in the context of asymmetric C-H activation. We disclose herein the conception a
Asymmetric synthesis of α-arylglycinols via additions of lithium methyl p-tolyl sulfoxide to N-(PMP)arylaldimines followed by 'non oxidative' Pummerer reaction
Bravo, Pierfrancesco,Capelli, Silvia,Crucianelli, Marcello,Guidetti, Maurizia,Markovsky, Andrey L.,Meille, Stefano V.,Soloshonok, Vadim A.,Sorochinsky, Alexander E.,Viani, Fiorenza,Zanda, Matteo
, p. 3025 - 3040 (2007/10/03)
The results presented in this paper demonstrate that the stereochemical outcome of the reversible additions of lithium (R)-methyl p-tolyl sulfoxide to N-arylidene-p-anisidines (N-PMP imines) is a function of a) the reaction conditions used and b) the electronic properties of the arylidene moiety on the starting imine. High kinetically controlled (2S,R(S)) diastereoselectivity (-70 °C) was achieved for additions of imines bearing relatively electron-rich N-arylidene groups, while an electron-deficient nature of this group was found to favor the opposite stereochemical outcome. On the other hand, the reactions run under thermodynamically controlled conditions (0 °C) afforded equimolar mixtures of the diastereomeric products regardless of the pattern of substitution on the starting imines. Enantiopure α-arylglycinols were readily synthesized by 'non-oxidative' Pummerer rearrangement of diastereomerically pure β-aryl-β-N-(acyl)aminoalkyl sulfoxides, prepared from the corresponding N-PMP derivatives.
Highly stereoselective reduction of acyclic α-sulfinyl ketimines: Synthesis of enantiomerically pure β-aminosulfoxides
Garcia Ruano, Jose L.,Cifuentes, Marta M.,Lorente, Antonio,Rodriguez Ramos, Jesus H.
, p. 4607 - 4618 (2007/10/03)
The DIBAL reduction of enantiomerically pure α-sulfinyl ketimines can be achieved almost completely stereoselectively under ZnX2 catalysis, regardless of the alkyl or aryl substituent at nitrogen and the aliphatic (cyclic or acyclic) or aromati
ASYMMETRIC ADDITIONS OF α-SULFOXIDE CARBANION ON IMINES
Ronan, B,Marchalin, S,Samuel, O,Kagan, H. B.
, p. 6101 - 6104 (2007/10/02)
The formation of the anion of methyl p-tolyl sulfoxide was studied in various experimental conditions.This allowed to get a very good control of diastereoselectivity during addition of the above carbanion on many imines.Various stereoisomerically pure ami
