ChemInform Abstract: Studies in Asymmetric Synthesis. Part 4. Studies in Lewis Acid and LiClO4 (or Nafion-H) Catalyzed Ionic Diels-Alder Reactions of Chiral and Achiral Olefinic Acetals Respectively.

ChemInform ◽  
2010 ◽  
Vol 30 (27) ◽  
pp. no-no
Author(s):  
R. Kumareswaran ◽  
Padma S. Vankar ◽  
M. Venkat Ram Reddy ◽  
Sangeeta V. Pitre ◽  
Raja Roy ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Diels Alder

Asymmetric synthesis of N-phenylethyl-2-phenyldecahydroquinolin-4-ones via Lewis acid catalyzed imino-Diels–Alder reaction

2000 ◽  
Vol 11 (12) ◽  
pp. 2509-2523 ◽  
Author(s):  
Renée Paugam ◽  
Emmanuelle Valenciennes ◽  
Linda Le Coz-Bardol ◽  
Jean-Christophe Garde ◽  
Lya Wartski ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Acid Catalyzed

Asymmetric synthesis of isoquinuclidines by Diels–Alder reaction of 1,2-dihydropyridine utilizing a chiral Lewis acid catalyst

Tetrahedron ◽  
2012 ◽  
Vol 68 (6) ◽  
pp. 1774-1781 ◽  
Author(s):  
Chigusa Seki ◽  
Masafumi Hirama ◽  
N.D.M. Romauli Hutabarat ◽  
Junko Takada ◽  
Chonticha Suttibut ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Acid Catalyst ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Chiral Lewis Acid ◽  
Lewis Acid Catalyst

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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