62269-46-9Relevant academic research and scientific papers
Synthesis of polycyclic structures by Diels-Alder reaction using inner- outer-ring 1,3-bis[trimethylsilyloxy]dienes
Sestelo, Jose Perez,Del Mar Real,Mourino, Antonio,Sarandeses, Luis A.
, p. 985 - 988 (1999)
In this paper we describe regioselective one-pot preparations of inner- outer-ring 1,3-bis[trimethylsilyloxy]dienes and their Diels-Alder reactions with electron-deficient dienophiles. The dienes were prepared in quantitative yield, and the Diels-Alder reactions proceeded smoothly, regioselectively and with good yields, allowing efficient construction of highly functionalized polycyclic skeletons such as naphthofurans, benzofurans and various carbocycles present in natural and non-natural products.
Synthesis of polycyclic structures by the Diels-Alder reaction of inner-outer-ring 1,3-bis(trimethylsilyloxy)dienes
Sestelo,Del Mar Real,Sarandeses
, p. 1395 - 1402 (2007/10/03)
A Diels-Alder reaction of novel inner-outer-ring 1,3-silyloxydienes 5-8 with a variety of dienophiles to afford highly functionalized polycyclic structures is reported. The inner-outer-ring 1,3-silyloxydienes 5-8 containing five- to seven-membered carbocyclic and heterocyclic rings were prepared in a single reaction vessel from 2-acetylcyclocarbonyls in quantitative yields. The Diels-Alder reaction with 1,4-benzoquinone (BQ), dimethyl acetylenedicarboxylate (DMAD), and methyl vinyl ketone (MVK) proceeded smoothly at room temperature, affording functionalized polycyclic naphthols, phenols, and enones with high regioselectivity and good yields (39-75%). Moreover, dienes 5-8 also reacted in a hetero-Diels-Alder reaction with benzaldehyde (BA) and N-benzylideneaniline (NBA) in the presence of catalytic amounts of ZnCI2, affording substituted polycyclic pyranones and pyridinones in good yields (40-93%). Overall, our synthetic strategy provides straightforward access to an interesting set of polycyclic structures useful for natural and nonnatural product synthesis.
Regioselective synthesis and acylation of cyclic bis-(trimethylsiloxy)- 1,3-dienes - New and versatile 1,3-dianion synthons
Langer, Peter,Schneider, Toni
, p. 497 - 500 (2007/10/03)
Cyclohexanone-derived bis-(trimethylsiloxy)-1,3-dienes were regioselectively prepared by the use of different silylating systems. These dienes represent new and versatile 1,3-dianion synthons in Lewis-acid catalyzed acylation reactions.
Domino reaction of 1,3-bis(trimethylsilyloxy)-1,3-dienes with oxalyl chloride: General and stereoselective synthesis of γ-alkylidenebutenolides
Langer, Peter,Schneider, Toni,Stoll, Martin
, p. 3204 - 3214 (2007/10/03)
The Lewis acid catalyzed cyclization of oxalyl chloride with 1,3-bis-(trimethylsilyloxy)-1,3-dienes 3, derived from 1,3-dicarbonyl compounds 1, provides a new and general approach for the synthesis of γ-alkylidenebutenolides 4, a pharmacologically and syn
FLASH VACUUM THERMOLYSIS OF β-KETO-TRIMETHYLSILYL-ENOL-ETHERS. SYNTHESIS OF ALLENIC AND FURANIC DERIVATIVES
Jullien, J.,Pechine, J. M.,Perez, F.,Piade, J. J.
, p. 1413 - 1416 (2007/10/02)
Thermolysis at 800 deg C of a series of β-keto-trimethylsilyl-enol-ethers allows the elimination of a trimethylsilanol molecule through a 1,5 rearrangement.The reduction products are furanic derivatives, which are obtained in often good yields through an allenic intermediate, which has been isolated.
