Progress on the Asymmetric Diels-Alder Reaction ofα,β-Unsaturated Carbonyl Compounds
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چکیده
منابع مشابه
Asymmetric Catalysis of Diels–Alder Reaction
The Diels–Alder (DA) reaction (or diene synthesis) between a diene and a dienophile generates two s bonds stereoselectively and up to four chiral centers in a single step to afford six-membered cyclic compounds. This cycloaddition reaction named after Professor Otto Paul Hermann Diels (1876–1954) and his student Kurt Alder (1902–1958) was discovered in 1928 during studies on the reaction of b...
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A one-pot procedure is described for using alpha,beta-unsaturated aldehydes as olefin equivalents in the Diels-Alder reaction. The method combines the normal electron demand cycloaddition with aldehyde dienophiles and the rhodium-catalyzed decarbonylation of aldehydes to afford cyclohexenes with no electron-withdrawing substituents. In this way, the aldehyde group serves as a traceless control ...
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Chiral dirhodium(II) carboxamidates are highly efficient catalysts for reactions between a variety of aldehydes and activated dienes. Catalyst loadings as low at 0.01 mol % have been realized with enantioselectivities up to 97%. Kinetic investigations reveal a pronounced electronic influence on the rate of the hetero-Diels-Alder reaction with a Hammett rho value of +1.9 (versus sigma(+)). Inhib...
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H etero-Diels-Alder Reaction, a,/?-Unsaturated Ketones, Styrenes Cycloadditions of 3-aryl-2-benzoyl-2-propenenitriles la,b to styrene (2a) and its methylor methoxy-substituted derivatives 2b-d proceed regioand diastereoselectively yielding cis and trans diastereoisomers of 2,4,6-triaryl-3,4-dihydro-2//-pyran-5-carbonitriles 3 and 4 in 59-72% yield. Cycloadducts cis-3 were the major products. Re...
متن کاملThe Diels-Alder Reaction: an Update
In this update on the Diels-Alder reaction we would like to present an overview on how this very important reaction has progressed in the last decade, since the last spate of monographs and reviews appeared in the literature, and which deal with the reaction in the overall sense. Initially we present the Diels-Alder reaction in a generalised form, much as discovered over seventy years ago, so t...
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ژورنال
عنوان ژورنال: Chinese Journal of Organic Chemistry
سال: 2016
ISSN: 0253-2786
DOI: 10.6023/cjoc201601027