use of the Diels-Alder reaction in asymmetric synthesis
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use of the Diels-Alder reaction in asymmetric synthesis

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Published .
Written in English


  • Diels-Alder reaction.

Book details:

Edition Notes

Statementby Dale Raymond Dei Rossi.
The Physical Object
Pagination[5], 56 leaves, bound :
Number of Pages56
ID Numbers
Open LibraryOL14229186M

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Although the retro Diels‐Alder reaction doesn't itself involve the asymmetric formation of chiral centers, this reaction can still be used as an important tool in organic synthesis, especially in the synthesis of some thermodynamically less stable compounds. The Diels-Alder reaction is a common pathway to synthesize high molecular weight polymers with different hierarchical structures including star, dendrimers, and graft copolymers [20].Furan-functional benzoxazine monomer (BA-fa) was synthesized using furfurylamine and bisphenol-A in dioxane [21].Then, the Diels-Alder reaction was carried out between BA-fa with bismaleimide as shown in . Synthesis of Optically Pure Spiro[cyclohexane-oxindoline] Derivatives via Catalytic Asymmetric Diels–Alder Reaction of Brassard-Type Diene with Methyleneindolines. The Journal of Organic Chemistry , 80 (17), DOI: /5bCited by:   Intramolecular hetero Diels–Alder reactions can also be planned in such a way that nitrogen is placed in the “dienophilic” component of the cycloaddition, and thus N-acylimines are precursors of example, compound () can be transformed into (±)-cryptopleurine through pyrolytic elimination to () followed by hetero Diels–Alder reaction and reduction (Scheme .

  The Diels–Alder [4+2] cycloaddition reaction 11 is arguably the most revered of all chemical reactiThe prototypical event (Fig. 1b), found in every introductory organic chemistry textbook, is the combination of 1,3-butadiene (5) as the 4π-component with ethylene (4) as the dienophile to give cyclohexene (6)–a product at the tetrahydrobenzene oxidation by: The Diels–Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which, arguably, has yet to be eclipsed by any other. Asymmetric C-O bond formations including epoxidation, dihydroxylation, and aminohydroxylation; Asymmetric synthesis using the Diels-Alder reaction and other cyclizations; Applications to the total synthesis of natural products; Use of enzymes in asymmetric synthesis. The asymmetric Diels-Alder reaction is one of the most powerful organic transformations and is a versatile tool for the synthesis of many bioactive natural : Johan Franzén.

The Diels-Alder reaction represents a promising tool for use in asymmetric synthesis. The reaction involves a rigid transition state that facilitates the formation of one diastereomeric transition state and is reversible. This satisfies two necessary criteria for asymmetric : Dei Rossi, Dale Raymond. Styrene copolymers containing various amounts of a novel comonomer bearing a pendant furan ring were synthesized and characterized before being submitted to Diels−Alder reactions with either a monomaleimide or a bismaleimide. Spectroscopic evidence, supported by data from model compounds, indicated that the resulting linear and cross-linked products contained extensive percentages of adduct. Advances in the Diels-Alder Reaction: Synthesis of (±)-Lycoridine and of Dolabellatrienone. Cyclic dienes such as 1 are reluctant participants in Diels-Alder cycloaddition. W. Dean Harman of the University of Virginia has shown (J. Am. Chem. Soc. , , ) . 1 Asymmetric Catalysis of Diels–Alder Reaction Haifeng Du and Kuiling Ding Introduction 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 cycloadditionFile Size: 1MB.