Samarium diiodide-induced intramolecular pinacol coupling of dinitrones: synthesis of cyclic cis-vicinal diamines

2005 ◽  
pp. 5402 ◽  
Author(s):  
Jean-Philippe Ebran ◽  
Rita G. Hazell ◽  
Troels Skrydstrup
Keyword(s):  
Samarium Diiodide ◽  
Pinacol Coupling ◽  
Vicinal Diamines

Samarium Diiodide-Induced Intramolecular Pinacol Coupling of Dinitrones: Synthesis of Cyclic cis-Vicinal Diamines.

ChemInform ◽  
2006 ◽  
Vol 37 (12) ◽  
Author(s):  
Jean-Philippe Ebran ◽  
Rita G. Hazell ◽  
Troels Skrydstrup
Keyword(s):  
Samarium Diiodide ◽  
Pinacol Coupling ◽  
Vicinal Diamines

Ligand Effects on the Diastereoselectivities of Samarium Diiodide Promoted Pinacol Coupling

1999 ◽  
Vol 1999 (3) ◽  
pp. 565-572 ◽  
Author(s):  
Henriette Lodberg Pedersen ◽  
Torben Birk Christensen ◽  
Rasmus Juel Enemærke ◽  
Kim Daasbjerg ◽  
Troels Skrydstrup
Keyword(s):  
Samarium Diiodide ◽  
Ligand Effects ◽  
Pinacol Coupling

ChemInform Abstract: Influence of a Dimetal Ion Binding Ferrocene Ligand on the Samarium Diiodide Promoted Pinacol Coupling Reaction.

ChemInform ◽  
2010 ◽  
Vol 31 (6) ◽  
pp. no-no
Author(s):  
Torben Birk Christensen ◽  
Ditte Riber ◽  
Kim Daasbjerg ◽  
Troels Skrydstrup
Keyword(s):  
Coupling Reaction ◽  
Ion Binding ◽  
Samarium Diiodide ◽  
Pinacol Coupling

scholarly journals Dual enantioselective control by heterocycles of (S)-indoline derivatives

2005 ◽  
Vol 77 (12) ◽  
pp. 2053-2059 ◽  
Author(s):  
Yong Hae Kim ◽  
Doo Young Jung ◽  
So Won Youn ◽  
Sam Min Kim ◽  
Doo Han Park
Keyword(s):  
Lewis Acid ◽  
Lewis Acids ◽  
Diels Alder ◽  
Samarium Diiodide ◽  
Coupling Reactions ◽  
Pinacol Coupling

Diastereo-and enantioselective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure (S,S)- or (R,R)-2,3-dialkyltartaric acid and derivatives can be synthesized. Diels-Alder cycloadditions of S-indoline chiral acrylamides with cyclopentadiene in the presence of Lewis acids proceed with high diastereofacial selectivity, giving either endo-R or endo-S products depending on Lewis acid and the structures of chiral dienophiles.

Asymmetric synthesis by stereocontrol

2001 ◽  
Vol 73 (2) ◽  
pp. 283-286 ◽  
Author(s):  
Yong Hae Kim ◽  
Sam Min Kim ◽  
So Won Youn
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Lewis Acids ◽  
Diels Alder ◽  
Samarium Diiodide ◽  
Coupling Reactions ◽  
Pinacol Coupling

Diels-Alder cycloadditions of S-indoline chiral acrylamides with cyclopentadiene in the presence of Lewis acids proceed with high diastereofacial selectivity, giving either endo-R or endo-S products depending on Lewis acid and the structures of chiral dienophiles. Diastereo- and enantioselective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure (S,S) - or (R,R) -2,3-dialkyltartaric acid and derivatives can be synthesized. Furthermore, it was demonstrated that α,β-unsaturated amides coupled with SmI2 to dimerized products containing two chiral carbons which were first obtained as the adjacent chiral carbons.

scholarly journals Stereocontrolled asymmetric synthesis

2000 ◽  
Vol 72 (9) ◽  
pp. 1691-1697 ◽  
Author(s):  
Yong Hae Kim ◽  
Sam Min Kim ◽  
Doo Han Park ◽  
So Won Youn
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Diels Alder ◽  
Samarium Diiodide ◽  
Coupling Reactions ◽  
Asymmetric Syntheses ◽  
Pinacol Coupling ◽  
First Time

Stereo differentiated asymmetric syntheses have been achieved by S-indoline derivations. Diels-Alder cycloadditions of S-indoline chiral acrylamides with cyclopentadiene proceed with high diastereofacial selectivity, giving either endo-R or endo-S products depending on Lewis acid and the structures of chiral dienophiles. Diastereo- and enantio-selective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure (S,S)- or (R,R)-2,3-dialkyltar-taric acid and derivatives can be synthesized for the first time depending on the structure of α-ketoamides.

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