27152-63-2Relevant articles and documents
Synthesis of 3-substituted 3-(trimethylsiloxy)pyrrolidines from β-aminoketones and lithium trimethylsilyldiazomethane
Hari, Yoshiyuki,Yokoyama, Takuya,Aoyama, Toyohiko
experimental part, p. 679 - 687 (2010/04/29)
Lithium trimethylsilyldiazomethane reacted with N-benzyl-β-aminoketones at -78 °C in THF to give 3-substituted 1-benzyl-3-(trimethylsiloxy)pyrrolidines in moderate to good yields.
Diastereoselective nickel-catalyzed reductive Aldol cyclizations using diethylzinc as the stoichiometric reductant: Scope and mechanistic insight
Joensuu, Pekka M.,Murray, Gordon J.,Fordyce, Euan A. F.,Luebbers, Thomas,Hon, Wai Lam
, p. 7328 - 7338 (2008/12/22)
In the presence of diethylzinc as a stoichiometric reductant, Ni(acac) 2 functions as an efficient precatalyst for the reductive aldol cyclization of α,β-unsaturated carbonyl compounds tethered to a ketone electrophile through an amide or an ester linkage. The reactions are tolerant of a wide range of substitution at both α,β-unsaturated carbonyl and ketone components and proceed smoothly to furnish β-hydroxylactams and β-hydroxylactones with generally high diastereoselectivities. A series of experiments, including deuterium-labeling studies, was carried out in an attempt to gain some insight into the possible reaction mechanisms that might be operative.
Diastereoselective cobalt-catalyzed alkylative aldol cyclizations using trialkylaluminum reagents
Rudkin, Mairi E.,Joensuu, Pekka M.,MacLachlan, William S.,Hon, Wai Lam
supporting information; experimental part, p. 2939 - 2942 (2009/04/18)
(Chemical Equation Presented) Co(acac)2?·2H2O serves as an effective precatalyst for alkylative aldol cyclizations of ?±,?2-unsaturated amides with ketones using trialkylaluminum reagents. These reactions provide ?2-hydroxylactams containing three contiguous stereocenters with high levels of diastereoselection. ? 2008 American Chemical Society.
Diastereoselective cobalt-catalyzed reductive aldol cyclizations using diethylzinc as the stoichiometric reductant
Lam, Hon Wai,Joensuu, Pekka M.,Murray, Gordon J.,Fordyce, Euan A. F.,Prieto, Oscar,Luebbers, Thomas
, p. 3729 - 3732 (2007/10/03)
Cobalt catalysis enables a new method for the generation of zinc enolates using diethylzinc to reduce α,β-unsaturated amides. This method has been applied to a high-yielding diastereoselective reductive aldol cyclization.
Synthesis of some novel 2-phenylpyridazino[4,5-b][1,5]thiazepines
Matyus, Peter,Zara-Kaczian, Erzsebet,Boros, Sandor,Boecskei, Zsolt
, p. 583 - 590 (2007/10/03)
Synthesis of some derivatives of the pyridazino[4,5-b][1,5]thiazepine ring system is reported. Thus, 5-benzyl-8-methyl-2-phenyl-2,3,4,5-tetrahydro-5H-pyridazino[4,5-b][1,5] thiazepin-9(8H)-one (5) was prepared by an intramolecular S-alkylation reaction, whereas the thiazepine ring of sulfone analogue 21, and that of the novel tricyclic pyrrolidino fused ring system 22 was elaborated by an intramolecular C-alkylation reaction. Unexpected formation of bicyclic pyrido- and thiazine fused pyridazine systems are also discussed.
3-Amino-5,6-dihydro-4H-thiopyran 1,1-Dioxides. Reactivity with Diethyl Azodicarboxylate and Some α,β-Unsaturated Ketones
Fatutta, Silvana,Pitacco, Giuliana,Valentin, Ennio
, p. 2111 - 2116 (2007/10/02)
The secondary enamines derived from 5,6-dihydro-2H-thiopyran-3(4H)-one 1,1-dioxide are in tautomeric equilibrium with their imine forms.With the title electrophiles, either they react at nitrogen or show the usual reactivity at the β-carbon atom of the en
EFFECT OF THE STRUCTURE OF THE REAGENTS ON THE FORMATION RATE OF ARYL VINYL KETONES IN THE REACTION OF AMINES WITH β-HALOGENOPROPIOPHENONES
Popov, A. F.,Piskunova, Zh. P.,Matvienko, V. N.
, p. 1918 - 1921 (2007/10/02)
The dependence of the formation rate of aryl vinyl ketones in the reaction of ring-substituted β-halogenopropiophenones with various amines on the structure of the reagents was investigated.By analysis of the obtained data it was concluded that the process takes place by an E2 mechanism through an anion-like transition state.
KINETICS AND MECHANISM OF REACTION OF AMINES WITH β-BROMOPROPIOPHENONE
Popov, A. F.,Piskunova, Z.,Matvienko, V. N.
, p. 1299 - 1302 (2007/10/02)
The reaction of β-bromopropiophenone with different amines in acetonitrile at 25 deg C was studied.It was found that in the case of primary and secondary amines, the end products of the reaction are β-aminopropiophenones, which form via the intermediate phenyl vinyl ketone.In the case of tertiary amines, the reaction ends at the stage of the formation of phenyl vinyl ketone.The reactivity of the amines in the formation of phenyl vinyl ketone is preferentially determined by their basicity.
