Design of an organocatalyst for the enantioselective Diels-Alder reaction with alpha-acyloxyacroleins.
@article{Ishihara2005DesignOA,
title={Design of an organocatalyst for the enantioselective Diels-Alder reaction with alpha-acyloxyacroleins.},
author={K. Ishihara and K. Nakano},
journal={Journal of the American Chemical Society},
year={2005},
volume={127 30},
pages={
10504-5
}
}We have realized the first enantioselective organocatalytic Diels-Alder reaction between alpha-substituted acroleins, such as alpha-acyloxyacroleins, and not only cyclic but also acyclic dienes. alpha-Acyloxyacroleins are useful as synthetic equivalents of alpha-haloacroleins. The present catalyst could be prepared in situ from pentafluorobenzenesulfonic acid (2.5-3.0 equiv) and chiral triamine (1 equiv) derived from H-l-Phe-l-Leu-N(CH2CH2)2. The enantioselective Diels-Alder reaction of 5… CONTINUE READING
Topics from this paper
148 Citations
Enantioselective Diels–Alder Reaction of α‐Acyloxyacroleins Catalyzed by Chiral 1,1′‐Binaphthyl‐2,2′‐diammonium Salts
- Chemistry
- 2006
- 57
Trienamine catalysis for asymmetric Diels-Alder reactions of 2,4-dienones: a theoretical investigation.
- Chemistry, Medicine
- Organic & biomolecular chemistry
- 2015
- 4
- PDF
The enantioselective, organocatalyzed Diels-Alder reaction of 2-vinylindoles with alpha,beta-unsaturated aldehydes: an efficient route to functionalized tetrahydrocarbazoles.
- Chemistry, Medicine
- Chemistry
- 2010
- 93
Organocatalytic, enantioselective intramolecular [6+2] cycloaddition reaction for the formation of tricyclopentanoids and insight on its mechanism from a computational study.
- Chemistry, Medicine
- Journal of the American Chemical Society
- 2011
- 36
Chiral 1,1'-binaphthyl-2,2'-diammonium salt catalysts for the enantioselective Diels-Alder reaction with alpha-acyloxyacroleins.
- Chemistry, Medicine
- Organic letters
- 2006
- 80
exo-selective asymmetric Diels-Alder reaction catalyzed by diamine salts as organocatalysts.
- Chemistry, Medicine
- Organic letters
- 2006
- 35
Enantioselective Diels-Alder reaction of 1,2-dihydropyridines with aldehydes using β-amino alcohol organocatalyst.
- Chemistry, Medicine
- The Journal of organic chemistry
- 2014
- 21
Asymmetric Diels-Alder reactions of alpha,beta-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether salt in the presence of water.
- Chemistry, Medicine
- Angewandte Chemie
- 2008
- 115