53178-46-4Relevant academic research and scientific papers
Substitution of HMPT by the Cyclic Urea DMPU as a Cosolvent for Highly Reactive Nucleophiles and Bases
Mukhopadhyay, Triptikumar,Seebach, Dieter
, p. 385 - 391 (1982)
The cyclic urea DMPU (N,N'-dimethyl-N,N'-propylene urea = 1,3-dimethyl-2-oxo-hexahydropyrimidine) is shown to exhibit the same effects as HMPT in oxirane-opening with Li-acetylide, in Wittig olefination, in the double deprotonation of a nitroalkane, in th
Quinuclidine N-oxide: A potential replacement for HMPA
O'Neil, Ian A.,Lai, Justine Y. Q.,Wynn, Duncan
, p. 59 - 60 (1999)
The use of quinuclidine N-oxide as a replacement for HMPA is described.
Replacement of HMPA in samarium diiodide promoted cyclizations and reactions of organolithium compounds
Berndt, Mathias,Hoelemann, Alexandra,Niermann, Andre,Bentz, Christoph,Zimmer, Reinhold,Reissig, Hans-Ulrich
experimental part, p. 1299 - 1302 (2012/04/04)
Tripyrrolidinophosphoric acid triamide (TPPA) can replace carcinogenic HMPA as a Lewis basic additive in many reactions involving samarium ketyls. In most cases, yields and selectivities of cyclizations of (het)aryl, alkenyl, and alkynyl ketones are simil
Synthesis of new chiral derivatives of N,N′-dimethylpropyleneurea (DMPU) and examination of their influence on the regio- and enantioselectivity of addition of 2-(1,3-dithianyl)lithium to cyclohex-2-en-1-one
Juaristi, Eusebio,Hernandez-Rodriguez, Marcos,Lopez-Ruiz, Heraclio,Avina, Judit,Munoz-Muniz, Omar,Hayakawa, Michiya,Seebach, Dieter
, p. 1999 - 2008 (2007/10/03)
The preparation of three new chiral derivatives of DMPU (N,N′-dimethylpropyleneurea) is described (Schemes 2-4); one type of derivative carries 1-phenylethyl or 1-cyclohexylethyl groups at the N-atoms of the tetrahydropyrimidin-2(1H)-one ring (2 and 4), a
Studies on the substituted 3-aminopropan-1-ol motif of lycoctonine class norditerpenid alkaloids: A novel route to 3-hydroxymethylcyclohex-2-enone
Doisy, Xavier,Blagbrough, Ian S.,Thomas, Noel F.,Potter, Barry V. L.
, p. 8525 - 8528 (2007/10/03)
Pursuing our interest in methyllcaconitine (MLA), we have designed a synthetic route to substituted ring-A of lycoctonine class norditerpenoid alkaloids. A novel synthesis of 3-hydroxymethylcyclohex-2-enone has been achieved starting from cyclohex-2-enone. Key reactions are: 1,2-addition of 1,3-dithiane followed by allylic rearrangement, 1,4-hydrocyanation, Wittig reaction and conversion into the substituted N-ethyl-3-aminopropan-1-ol motif of these neopentyl-like alcohols.
A SIMPLE SYNTHESIS OF γ-HYDROXY-α,β-UNSATURATED ALDEHYDES
Ranu, Brindaban C.,Sarkar, Dipak C.
, p. 155 - 160 (2007/10/02)
A convenient method has been developed for the synthesis of γ-hydroxy-α,β-unsaturated aldehydes with one-carbon homologation from α,β-unsaturated ketones.
A Comparison of the Reactions of lithium with α,β-Unsaturated Ketones and Those of Other Acyl Anion Equivalents Containing Sulfur
Ager, David J.,East, Michael B.
, p. 3983 - 3992 (2007/10/02)
The factors influencing the site of attack of lithium (1) with enones were investigated.Cyclohexenone (2) was chosen as a model compound, and conjugate addition occurred in THF-HMPA or DME; this mode of addition was also promoted by a potassium counterion.When the reaction was carried out with other enones, conjugate addition in THF-HMPA or DME was only observed if the β-position or the α,β-unsaturated ketone was not disubstituted. 1,4-Addition of 1 could be accomplished by preparation of the cuprate.The use of this approach was illustrated by a preparation of 4,4-dimethylcyclopent-2-en-1-one (28).For determination of the influence of DME on the regiochemical control of the addition of other sulfur-containing anions to enones, the study was extended to the anions derived from 1,3-dithian (29), bis(phenylthio)methane (30), bis(phenylthio)(trimethylsilyl)methane (35), and bis(trimethylsilyl)(phenylthio)methane (36).With these anions, DME did not promote conjugate addition to any significant extent.
CONJUGATE (1,4) ADDITION OF HETEROCYCLIC ACYL ANION EQUIVALENTS TO CYCLIC α-ENONES IN THE PRESENCE OF HEXAMETHYLPHOSPHORIC TRIAMIDE: A GENERAL REACTION
Brown, Charles Allan,Chapa, O.,Yamaichi, A.
, p. 187 - 189 (2007/10/02)
Heterocyclic dithiaorganolithium reagents react with cyclic α-enones in THF to yield only products of carbonyl (1,2) addition; in the presence of 2.0 equivalents of hexamethylphosphoric triamide, the addition proceeds to give nearly exclusively the produc
