Efficient Synthesis of (±)-N-Boc-pregabalin via Hetero-Diels-Alder Addition of Methyl 3-Nitrosoacrylate to Ethyl Vinyl Ether

Heterocycles ◽  
2007 ◽  
Vol 71 (5) ◽  
pp. 1127 ◽  
Author(s):  
John K. Gallos ◽  
Elli S. Alexandraki ◽  
Christos I. Stathakis
Keyword(s):  
Vinyl Ether ◽  
Diels Alder ◽  
Ethyl Vinyl Ether ◽  
Efficient Synthesis ◽  
Ethyl Vinyl

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

Synthesis of (±)-Crispine A via a Nitrosoalkene Hetero-Diels-Alder Addition to Ethyl Vinyl Ether

Synthesis ◽  
2010 ◽  
Vol 2011 (01) ◽  
pp. 142-146 ◽  
Author(s):  
John Gallos ◽  
Efthymia Yioti ◽  
Ioulia Mati ◽  
Athanassios Arvanitidis ◽  
Zoe Massen ◽  
...  
Keyword(s):  
Vinyl Ether ◽  
Diels Alder ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl

A Facile Synthesis of 2,6-Dideoxy 6,6,6-Trifluorinated Carbohydrate Analogues

1998 ◽  
Vol 51 (7) ◽  
pp. 545 ◽  
Author(s):  
Colin M. Hayman ◽  
David S. Larsen ◽  
Sally Brooker
Keyword(s):  
Vinyl Ether ◽  
Boron Trifluoride Etherate ◽  
Diels Alder ◽  
Ethyl Vinyl Ether ◽  
Similar Reaction ◽  
X Ray Diffraction ◽  
Facile Synthesis ◽  
Ethyl Vinyl ◽  
X Ray ◽  
Structural Assignment

The syntheses of 2,6-dideoxy-6,6,6-trifluoro-DL-arabino-hexose (4) and the corresponding glycoside, ethyl 2,6-dideoxy-6,6,6-trifluoro-DL-arabino-hexopyranoside (11), are described. The key step in the synthesis of (4) involved the Lewis acid catalysed hetero-Diels–Alder reactions of (E)-4-benzyloxy-1,1,1-trifluorobut-3-en-2-one and benzyl vinyl ether. Hydroboration of the resulting cycloadduct, and hydrogenylitic debenzylation gave (4) in a 59% overall yield. The ethyl glycoside (11) was prepared in a similar manner from ethyl vinyl ether. A single-crystal X-ray diffraction study confirmed the structural assignment of (11). The O-glycosides (17) and (18) were formed from the boron trifluoride etherate promoted reaction of the per-acetate of (4), i.e. (16), and 2-naphthol. However, a similar reaction between 5-hydroxy-1,4-dimethoxynaphthalene and (16) gave the disubstituted C-glycoside (19) in 52% yield.

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).

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