scholarly journals Enantioselective Friedel-Crafts Reaction of Indoles with Isatins Catalyzed by Cinchona Alkaloid Silyl Ether Derivative

2021 ◽  
Vol 41 (3) ◽  
pp. 1187
Author(s):  
Junwei Zhang ◽  
Hao Wu ◽  
Weixin Zhang ◽  
Liming Wang ◽  
Ying Jin
Keyword(s):  
Cinchona Alkaloid ◽  
Silyl Ether ◽  
Ether Derivative

Cinchona Alkaloid-Silyl Ether Derivatives as Organocatalysts for Asymmetric “Interrupted” Feist-Bénary Reaction

2013 ◽  
Vol 864-867 ◽  
pp. 456-459
Author(s):  
Ying Jin ◽  
Sheng Chang ◽  
Tian Yi Zhang ◽  
Bo Feng
Keyword(s):  
Enantiomeric Excess ◽  
Cinchona Alkaloid ◽  
Silyl Ether ◽  
Ethyl Bromopyruvate

Four cinchona alkaloid-silyl ether derivatives have been used to catalyze the asymmetric “interrupted” Feist-Bénary reaction of ethyl bromopyruvate/substituted bromo-ketoesters and 1,3-Cyclohexadione. The corresponding hydroxydihydrofurans have been obtained in excellent yields (85-96%) with high enantiomeric excess (ee) values of up to 90%.

Intermolecular Diels-Alder reactions of 3-vinylcyclohex-2-en-1-ol and a silyl ether derivative

1988 ◽  
Vol 53 (4) ◽  
pp. 901-904 ◽  
Author(s):  
Lucjan Strekowski ◽  
Sukbin Kong ◽  
Merle A. Battiste
Keyword(s):  
Diels Alder ◽  
Silyl Ether ◽  
Ether Derivative

On the Chemistry of Ingenol, III [1] Synthesis of 3-Deoxy-3-oxoingenol, Some 5-Esters and of Ethers and Acetals of Ingenol

1982 ◽  
Vol 37 (12) ◽  
pp. 1640-1647 ◽  
Author(s):  
Bernd Sorg ◽  
Erich Hecker
Keyword(s):  
Good Yield ◽  
Protecting Groups ◽  
Silyl Ether ◽  
Subsequent Removal ◽  
Mouse Ear

3-Deoxy-3-oxoingenol (3) was prepared from ingenol-5,20-acetonide (25) by oxidation and subsequent removal of the acetonide. 3 was acylated to give homologous 5,20-diacylates 5-9. From these the 5-monoacylates 14, 15 and 17 were obtained in only moderate yields. Therefore the 20-silyl ether 10 (prepared from 3) was acylated. After smooth removal of the silyl ether the homologous 5-acylates 16. 18 and 19 resulted in good yield. The 5,20-dibutyrate 6 and all 5-acylates prepared (14-19) showed no irritant activity on the mouse ear. The 3-oxo-5-acylates 14-19 could not be reduced to give ingenol-5-acylates (24). Therefore various ingenol derivatives, 29-32, with suitable protected hydroxyl functions as well as the corresponding 5-clecanoates 35-38 were synthesized. The protecting groups of the derivatives 35-38 could however not be cleaved off to yield ingenol-5- decanoate (24)

Reductive cleavage mechanism of diphenyl ether and apparent ipso trapping of an intermediate radical anion with a silyl ether

1982 ◽  
Vol 47 (22) ◽  
pp. 4250-4254 ◽  
Author(s):  
Kundanbhai M. Patel ◽  
Richard J. Baltisberger ◽  
Virgil I. Stenberg ◽  
Neil F. Woolsey
Keyword(s):  
Radical Anion ◽  
Diphenyl Ether ◽  
Reductive Cleavage ◽  
Silyl Ether ◽  
Intermediate Radical
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