Straightforward route to 2- and 3-formyl hex-1- and -2-enopyranosides and their highly stereoselective hetero Diels–Alder reaction with ethyl vinyl ether

1988 ◽  
pp. 514-515 ◽  
Author(s):  
J. Cristobal Lopez ◽  
Eric Lameignere ◽  
Gabor Lukacs
Keyword(s):  
Vinyl Ether ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl ◽  
Diels Alder Reaction

Lanthanide catalysts for the hetero Diels–Alder reaction: effect of ligand structure and acidity

1997 ◽  
Vol 75 (8) ◽  
pp. 1047-1054 ◽  
Author(s):  
Claude Spino ◽  
Laurel L. Clouston ◽  
David J. Berg
Keyword(s):  
Catalytic Activity ◽  
Vinyl Ether ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl ◽  
Catalytic Activities ◽  
Ligand Structure ◽  
Bite Angle ◽  
Diels Alder Reaction

A series of yttrium, ytterbium, and lanthanum hexa-or heptacoordinate complexes were prepared and their catalytic activities tested in the hetero Diels–Alder reaction between crotonaldehyde and ethyl vinyl ether. It was found that a pKa below 7 of the ligand was necessary but not sufficient for catalytic activity. It was determined that the ligand should possess a perfluoromethyl-β-diketonate functionality. Other factors such as bite angle and hinging motion may also play a determining role. Keywords: lanthanide, catalyst, hetero Dielsis–Alder, yttrium, ytterbium, lanthanum.

Diels–Alder reaction of fused pyran-2-ones with ethyl vinyl ether

2012 ◽  
Vol 143 (5) ◽  
pp. 771-777 ◽  
Author(s):  
Amadej Juranovič ◽  
Krištof Kranjc ◽  
Slovenko Polanc ◽  
Franc Perdih ◽  
Marijan Kočevar
Keyword(s):  
Vinyl Ether ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl ◽  
Diels Alder Reaction

ChemInform Abstract: Diels-Alder Reaction of Fused Pyran-2-ones with Ethyl Vinyl Ether.

ChemInform ◽  
2012 ◽  
Vol 43 (33) ◽  
pp. no-no
Author(s):  
Amadej Juranovic ◽  
Kristof Kranjc ◽  
Slovenko Polanc ◽  
Franc Perdih ◽  
Marijan Kocevar
Keyword(s):  
Vinyl Ether ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl ◽  
Diels Alder Reaction

ChemInform Abstract: Stereoselective hetero-Diels-Alder Reaction of 3-Nitro-2-trihalomethyl-2H-chromenes with 2,3-Dihydrofuran and Ethyl Vinyl Ether under Solvent-Free Conditions.

ChemInform ◽  
2010 ◽  
Vol 41 (24) ◽  
pp. no-no
Author(s):  
Vladislav Yu. Korotaev ◽  
Vyacheslav Ya. Sosnovskikh ◽  
Mikhail A. Barabanov ◽  
Evgeniya S. Yasnova ◽  
Marina A. Ezhikova ◽  
...  
Keyword(s):  
Vinyl Ether ◽  
Alder Reaction ◽  
Diels Alder ◽  
Solvent Free ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl ◽  
Diels Alder Reaction ◽  
Solvent Free Conditions

A Stereoselective Synthesis of 2,6-Dideoxy-6,6,6-trifluoro-arabino-hexoses via an Asymmetric Diels - Alder Strategy

1999 ◽  
Vol 52 (10) ◽  
pp. 921 ◽  
Author(s):  
Colin M. Hayman ◽  
Lyall R. Hanton ◽  
David S. Larsen ◽  
Jenness M. Guthrie
Keyword(s):  
Vinyl Ether ◽  
Stereoselective Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Crystallographic Structure ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Enantioselective Syntheses

The enantioselective syntheses of each enantiomer of ethyl 2,6-dideoxy-6,6,6-trifluoro-β-arabino-hexopyranoside (3) and of 2,6-dideoxy-6,6,6-trifluoro-arabino-hexose (4) are described. The key step in the approach is the inverse electron demand Lewis acid catalysed Diels–Alder reaction of the heterodiene (E)-1,1,1-trifluoro-4-[(1R)-1- phenylethoxy]but-3-en-2-one (5) and either ethyl vinyl ether (7a) or benzyl vinyl ether (7b). The titanium(IV) chloride catalysed cycloadditions at low temperature displayed high endo-selectivity and modest diastereofacial selectivity. Hydroboration of the mixture of the cis-cycloadducts (8a) afforded the separable diastereoisomers (9a) and (10a). Hydrogenolysis of (9a) gave ethyl 2,6-dideoxy-6,6,6-trifluoro-β-L-arabino-hexopyranoside (+)-(3), and of (10a) gave the corresponding D-glycoside (−)-(3). Similarly, hydroboration of the cis-cycloadducts (8b) gave the protected benzyl glycosides (9b) and (10b). Hydrogenolysis of each gave 2,6-dideoxy-6,6,6-trifluoro-L-arabino-hexopyranose (−)-(4) and the corresponding D-sugar (+)-(4) respectively. The absolute configurations of fluorinated carbohydrates (+)- and (−)-(3) were determined by comparison of their molar rotations with those of the parent glycosides. These assignments were confirmed by an X-ray crystallographic structure determination of the glycoside (9a).

Stereoselective hetero-Diels–Alder reaction of 3-nitro-2-trihalomethyl-2H-chromenes with 2,3-dihydrofuran and ethyl vinyl ether under solvent-free conditions

Tetrahedron ◽  
2010 ◽  
Vol 66 (6) ◽  
pp. 1404-1409 ◽  
Author(s):  
Vladislav Yu. Korotaev ◽  
Vyacheslav Ya. Sosnovskikh ◽  
Mikhail A. Barabanov ◽  
Evgeniya S. Yasnova ◽  
Marina A. Ezhikova ◽  
...  
Keyword(s):  
Vinyl Ether ◽  
Alder Reaction ◽  
Diels Alder ◽  
Solvent Free ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl ◽  
Diels Alder Reaction ◽  
Solvent Free Conditions
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