68984-52-1Relevant academic research and scientific papers
The regioselectivity of addition of organolithium reagents to enones and enals: The role of HMPA
Sikorski,Reich
, p. 6527 - 6535 (2001)
The role of polar solvents (particularly HMPA) in controlling the ratio of 1.2 to 1,4 addition of sulfur-substituted organolithium reagents to cyclohexenones and hexenal was studied. Low-temperature, multinuclear NMR studies provided quantitative informat
Synthese totale de la (+/-) desoxy-11 daunomycinone et d'analogues a cycle D modifie
Abdallah, Abdallah Awad,Gesson, Jean-Pierre,Jacquesy, Jean-Claude,Mondon, Martine
, p. 93 - 100 (2007/10/02)
The total synthesis of (+/-) 11-deoxy Daunomycinone, the aglycon of a recently isolated antitumor anthracycline by two differents routes starting either from Hagemann's Ester (Method A) or from 2-cyclohexen 1-one (Method B) is described.The building of th
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
Alkoxide-Promoted Rearrangements of 1,3-Dithianes
Wilson, Stephen R.,Misra, Raj N.,Georgiadis, Gregory M.
, p. 2460 - 2468 (2007/10/02)
The allylic alcohols formed from 1,2-addition of 2-lithio-1,3-dithianes to α,β-unsaturated ketones have been shown to undergo rearrangement to afford their respective Michael-addition products upon treatment with KH in HMPA/THF in some cases.The major side reaction and in some instances the sole reaction pathway was fragmentation.The rearrangement was applied to a two-carbon macrocyclic ring-expansion strategy which is illustrated in a synthesis of DL-muscone, a 15-membered-ring ketone, from cyclotridecanone.Attempts to induce a similar rearrangement by replacing the 1,3-dithiane group with a thiophenyl or 1,3-dithiolane group proved unsuccessful.
