ChemInform Abstract: A Convenient Synthetic Route to Functionalized 5-Trifluoroacetyl-6-trifluoromethyl-3,4-dihydro-2H-pyrans: Hetero-Diels-Alder Reaction of β,β-Bis(trifluoroacetyl)vinyl Ethers with Electron-Rich Alkenes.

ChemInform ◽  
1990 ◽  
Vol 21 (39) ◽  
Author(s):  
M. HOJO ◽  
R. MASUDA ◽  
E. OKADA
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Route ◽  
Vinyl Ethers ◽  
Diels Alder Reaction

scholarly journals A new synthetic route to methyl (-)-shikimate by asymmetric diels-alder reaction of (S)s-3-(2-pyridylsulfinyl)acrylate.

1988 ◽  
Vol 36 (8) ◽  
pp. 3213-3215 ◽  
Author(s):  
Tamiko Takahashi ◽  
Toshie Namiki ◽  
Yoshio Takeuchi ◽  
Toru Koizumi
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Route ◽  
Diels Alder Reaction

A common synthetic route to homochiral tetracycles related to pillaromycinone and premithramycinone

2011 ◽  
Vol 89 (12) ◽  
pp. 1457-1468 ◽  
Author(s):  
Bryan Hill ◽  
Robert Jordan ◽  
Yang Qu ◽  
Abdeljalil Assoud ◽  
Russell Rodrigo
Keyword(s):  
Double Bond ◽  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Route ◽  
Homogeneous Hydrogenation ◽  
Diels Alder Reaction

Homochiral AB segments for (+)- and (–)-pillaromycinone were prepared in 11 steps from 2-acetylfuran. The synthesis featured an intramolecular Diels–Alder reaction of a 2,5-disubstituted furan and a hydroxyl-directed homogeneous hydrogenation of the tetrasubstituted alkene double bond of two enones. The CD segment was attached by a modified Staunton–Weinreb annulation to produce the desired homochiral tetracycle 21c related to (+)-pillaromycinone. An unusual acetonide migration enabled the synthesis of a tetracyclic model for premithramycinone.

Density functional theory computational study on Diels–Alder reactions of cyclopentadiene with selected vinylsilanes and methylenecyclopropane

2011 ◽  
Vol 89 (3) ◽  
pp. 409-414 ◽  
Author(s):  
Nick Henry Werstiuk ◽  
Wojciech Sokol
Keyword(s):  
Density Functional Theory ◽  
Dft Calculations ◽  
Density Functional ◽  
Computational Study ◽  
Alder Reaction ◽  
Diels Alder ◽  
Rate Data ◽  
Synthetic Route ◽  
Functional Theory ◽  
Diels Alder Reaction

Aimed at predicting relative reactivities, density functional theory (DFT) calculations were carried out on a series of Diels–Alder reactions involving silylvinyl derivatives reacting with cyclopentadiene as part of a synthetic research project. Using three reactions for which experimental rate data are available to calibrate our calculations, we computationally pinpointed the best synthetic route to bicyclo[2.2.1]hept-5-ene-2,2-diylbis(trimethylsilane) (1). The synthesis begins with the Diels–Alder reaction of cyclopentadiene (2) with commercially available (1-bromovinyl)trimethylsilane (6).

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