Modular DNA-based hybrid catalysts as a toolbox for enantioselective hydration of α,β-unsaturated ketones

2019 ◽  
Vol 17 (9) ◽  
pp. 2548-2553 ◽  
Author(s):  
Ji Hye Yum ◽  
Soyoung Park ◽  
Ryota Hiraga ◽  
Izumi Okamura ◽  
Shunta Notsu ◽  
...  
Keyword(s):  
Double Bond ◽  
Direct Access ◽  
Chiral Alcohols ◽  
Unsaturated Ketones ◽  
Hybrid Catalysts ◽  
Carbon Double Bond ◽  
Direct Addition

The direct addition of water to a carbon–carbon double bond remains a challenge, but such a reaction is essential for the development of efficient catalysts that enable direct access to chiral alcohols.

scholarly journals Chemoselective and metal-free reduction of α,β-unsaturated ketones by in situ produced benzeneselenol from O-(tert-butyl) Se-phenyl selenocarbonate

RSC Advances ◽  
2020 ◽  
Vol 10 (56) ◽  
pp. 33706-33717
Author(s):  
Andrea Temperini ◽  
Marco Ballarotto ◽  
Carlo Siciliano
Keyword(s):  
Double Bond ◽  
Hydrochloric Acid ◽  
Unsaturated Ketones ◽  
Metal Free ◽  
Tert Butyl ◽  
Carbon Double Bond

The carbon–carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol.

Silyl-substituted α,β-Unsaturated Ketones from the Reaction of Silylvinylmetallic Reagents with Acid Anhydrides

1973 ◽  
Vol 51 (12) ◽  
pp. 2024-2032 ◽  
Author(s):  
A. G. Brook ◽  
J. M. Duff
Keyword(s):  
Double Bond ◽  
Low Temperatures ◽  
Silyl Group ◽  
Unsaturated Ketones ◽  
Carbon Double Bond ◽  
Benzoic Anhydride ◽  
Acid Anhydrides ◽  
By Products

The reactions of a series of silyl-substituted vinylmetallic reagents with acetic and benzoic anhydride have been investigated as a general route to α,β-unsaturated ketones having a silyl group attached to the carbon–carbon double bond. The reaction has been found to be generally applicable for acetyl derivatives provided low temperatures are used but the reaction with benzoic anhydride gives poorer results. The i.r. and u.v. spectra of the ketones are discussed. The characterization of novel 1,4-dienes obtained as by-products in the syntheses is also described.

Asymmetric reduction of α,β-unsaturated ketones with a carbon-carbon double-bond reductase from baker's yeast

1998 ◽  
Vol 39 (29) ◽  
pp. 5225-5228 ◽  
Author(s):  
Yasushi Kawai ◽  
Motoko Hayashi ◽  
Yoshikazu Inaba ◽  
Kentarou Saitou ◽  
Atsuyoshi Ohno
Keyword(s):  
Double Bond ◽  
Asymmetric Reduction ◽  
Baker’S Yeast ◽  
Baker's Yeast ◽  
Unsaturated Ketones ◽  
Carbon Double Bond ◽  
Double Bond Reductase

Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Synthesis ◽  
2021 ◽  
Author(s):  
Dmitrii L. Obydennov ◽  
Vyacheslav D. Steben’kov ◽  
Konstantin L. Obydennov ◽  
Sergey A. Usachev ◽  
Vladimir S. Moshkin ◽  
...  
Keyword(s):  
Double Bond ◽  
Ring Opening ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Computational Studies ◽  
Carbon Double Bond ◽  
Reactivity Indexes ◽  
Reaction Proceeds

Abstract4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

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