Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives

2018 ◽  
Vol 16 (7) ◽  
pp. 1079-1082 ◽  
Author(s):  
Jian Qiang Huang ◽  
Zackaria Nairoukh ◽  
Ilan Marek
Keyword(s):  
Carbonyl Compounds ◽  
Diastereoselective Synthesis ◽  
Carbonyl Derivatives ◽  
Electrophilic Fluorination

A highly diastereoselective synthesis of tertiary α-fluoro carbonyl compounds is reported in only two chemical steps from a simple alkyne through the reaction of stereodefined fully substituted silyl ketene hemiaminal derivatives with Selectfluor.

scholarly journals Transition Metal-Catalyzed α-Position Carbon–Carbon Bond Formations of Carbonyl Derivatives

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 861 ◽  
Author(s):  
Ha-Eun Lee ◽  
Dopil Kim ◽  
Ahrom You ◽  
Myung Hwan Park ◽  
Min Kim ◽  
...  
Keyword(s):  
Transition Metal ◽  
Carbonyl Compounds ◽  
Bond Formation ◽  
Chiral Ligand ◽  
Catalytic Systems ◽  
Carbon Bond ◽  
Carbonyl Derivatives ◽  
Carbon Carbon Bond ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

α-Functionalization of carbonyl compounds in organic synthesis has traditionally been accomplished via classical enolate chemistry. As α-functionalized carbonyl moieties are ubiquitous in biologically and pharmaceutically valuable molecules, catalytic α-alkylations have been extensively studied, yielding a plethora of practical and efficient methodologies. Moreover, stereoselective carbon–carbon bond formation at the α-position of achiral carbonyl compounds has been achieved by using various transition metal–chiral ligand complexes. This review describes recent advances—in the last 20 years and especially focusing on the last 10 years—in transition metal-catalyzed α-alkylations of carbonyl compounds, such as aldehydes, ketones, imines, esters, and amides and in efficient carbon–carbon bond formations. Active catalytic species and ligand design are discussed, and mechanistic insights are presented. In addition, recently developed photo-redox catalytic systems for α-alkylations are described as a versatile synthetic tool for the synthesis of chiral carbonyl-bearing molecules.

scholarly journals An Unprecedented Straightforward Synthesis of Chiral Pyrrolo[3,4-b]quinolone and Pyrrolo[3,2-b]quinolone Backbones Starting fromtrans-4-Hydroxy-L-proline

2016 ◽  
Vol 2016 ◽  
pp. 1-5
Author(s):  
Sébastien Comesse ◽  
Adam Daïch
Keyword(s):  
Carbonyl Compounds ◽  
Good Yield ◽  
Anticancer Activities ◽  
Carbonyl Derivatives

The straightforward synthesis of pyrrolo[3,4-b]quinolone and pyrrolo[3,2-b]quinolone backbones, which can be found in molecules exhibiting anticancer activities, is presented. The key step of the process is an efficient and unprecedented Friedländer condensation between an oxoproline carbamate, obtained in 3 steps and good yield starting from commercially available and relatively cheaptrans-4-hydroxy-L-proline, and various 2-amino-substituted carbonyl derivatives. It was demonstrated that the formation of the two possible regioisomers was fully triggered by both the R substituent onto the 2-amino-substituted carbonyl compounds and the ester function onto the oxoproline carbamate. Thus, in some cases, a complete regiocontrol for the Friedländer reaction could be attained.

Enantioselective and Diastereoselective Synthesis of Fluorinated Dipeptides by Late Electrophilic Fluorination.

ChemInform ◽  
2005 ◽  
Vol 36 (44) ◽  
Author(s):  
Barbara Mohar ◽  
Damjan Sterk ◽  
Laurent Ferron ◽  
Dominique Cahard
Keyword(s):  
Diastereoselective Synthesis ◽  
Electrophilic Fluorination

ChemInform Abstract: SmI2-Mediated 3-exo-trig Cyclization of β,γ-Unsaturated Carbonyl Compounds: Diastereoselective Synthesis of Cyclopropanols.

ChemInform ◽  
2010 ◽  
Vol 42 (2) ◽  
pp. no-no
Author(s):  
Mar Martin-Fontecha ◽  
Antonia R. Agarrabeitia ◽  
Maria J. Ortiz ◽  
Diego Armesto
Keyword(s):  
Carbonyl Compounds ◽  
Diastereoselective Synthesis
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