Furanyl cyclic amines: a diastereoselective synthesis of 2,6-syn-disubstituted piperidines under thermodynamic control

2012 ◽  
Vol 10 (12) ◽  
pp. 2392 ◽  
Author(s):  
Matthew O'Brien ◽  
Andrew Leach ◽  
Roly J. Armstrong ◽  
Keting Chong ◽  
Ross Sheridan
Keyword(s):  
Diastereoselective Synthesis ◽  
Thermodynamic Control ◽  
Cyclic Amines

ChemInform Abstract: Furanyl Cyclic Amines: A Diastereoselective Synthesis of 2,6-syn-Disubstituted Piperidines under Thermodynamic Control.

ChemInform ◽  
2012 ◽  
Vol 43 (33) ◽  
pp. no-no
Author(s):  
Matthew O'Brien ◽  
Andrew Leach ◽  
Roly J. Armstrong ◽  
Keting Chong ◽  
Ross Sheridan
Keyword(s):  
Diastereoselective Synthesis ◽  
Thermodynamic Control ◽  
Cyclic Amines

Catalyst-Controlled Diastereoselective Synthesis of Cyclic Amines via C-H Functionalization

2017 ◽  
Author(s):  
Sailu Munnuri ◽  
Adeniyi Michael Adebesin ◽  
Mahesh P Paudyal ◽  
Muhammed Yousufuddin ◽  
Alfonso Dalipe ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Cyclic Amines

Stereodivergent Alkyne Hydrofluorination Using a Simple Practical Reagent

2020 ◽  
Author(s):  
Rui Guo ◽  
Xiaotian Qi ◽  
Hengye Xiang ◽  
Paul Geaneoates ◽  
Ruihan Wang ◽  
...  
Keyword(s):  
Bond Formation ◽  
Biologically Active ◽  
Dft Studies ◽  
Thermodynamic Control ◽  
Important Goal ◽  
Peptide Bonds ◽  
Metal Free ◽  
Vinyl Cation ◽  
E And Z Isomers ◽  
Vinyl Fluorides

Vinyl fluorides play an important role in drug development as they serve as bioisosteres for peptide bonds and are found in a range of biologically active molecules. The discovery of safe, general and practical procedures to prepare vinyl fluorides remains an important goal and challenge for synthetic chemistry. Here we introduce an inexpensive and easily-handled reagent and report simple, scalable, and metal-free protocols for the regioselective and stereodivergent hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These conditions were suitable for a diverse collection of alkynes, including several highly-functionalized pharmaceutical derivatives. Mechanistic and DFT studies support C–F bond formation through a vinyl cation intermediate, with the (E)- and (Z)-hydrofluorination products forming under kinetic and thermodynamic control, respectively.<br>

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