86971-64-4Relevant academic research and scientific papers
A General and Robust Method for the Preparation of (E)- and (Z)-Stereodefined Fully Substituted Enol Tosylates: Promising Cross-Coupling Partners
Ashida, Yuichiro,Sato, Yuka,Honda, Atsushi,Nakatsuji, Hidefumi,Tanabe, Yoo
supporting information, p. 4072 - 4080 (2016/11/26)
A robust method for preparing (E)- and (Z)-stereodefined fully substituted enol tosylates is described. α-Substituted β-keto esters undergo (E)-selective enol tosylations using TsCl-Me2N(CH2)6NMe2 as the reagent (method A, 13 examples; 63-96%) and (Z)-selective enol tosylations using TsCl-TMEDA-LiCl as the reagent (method B, 13 examples; 62-99%). A plausible mechanism for the (E)- and (Z)-enol tosylation selectivity is proposed. A 1H NMR monitoring experiment revealed that TsCl coupled with TMEDA formed a simple N-sulfonylammonium intermediate.
Reductive Ti-crossed Claisen condensation between methyl α-bromocarboxylates and acid chlorides utilizing a TiCl 4-PPh3-N-methylimidazole reagent
Iida, Akira,Nakazawa, Syogo,Nakatsuji, Hidefumi,Misaki, Tomonori,Tanabe, Yoo
, p. 48 - 49 (2007/10/03)
Reductive Ti-crossed Claisen condensation between methyl α-bromocarboxylates and acid chlorides utilizing a TiCl 4-PPh3-N-methylimidazole reagent proceeded smoothly to give the α-monosubstituted and thermodynamically unfavorable α,α-
Stereoselective synthesis of new chiral N-tertiary tetrasubstituted β-enamino ester piperidines through an ammonia-catalyzed process
Calvet-Vitale, Sandrine,Vanucci-Bacque, Corinne,Fargeau-Bellassoued, Marie-Claude,Lhommet, Gerard
, p. 2071 - 2077 (2007/10/03)
We report here two approaches for the preparation of new N-substituted β-enamino ester piperidines featuring an exocyclic tetrasubstituted double bond, based either on the direct alkylation of piperidine β-enamino esters bearing an exocyclic trisubstitute
New method of zinc activation by electrochemistry: synthetic applications to the Blaise reaction
Zylber, N.,Zylber, J.,Rollin, Y.,Dunach, E.,Perichon, J.
, p. 1 - 4 (2007/10/02)
A new electrochemical zinc metal activation method based on the cathodic reduction of a catalytic amount of zinc bromide in the presence of a zinc anode is described.This procedure is applied to the coupling of α-bromoesters with nitriles, and affords β-ketoesters in good yield.
