New generation and intramolecular Diels-Alder reaction of isobenzofurans: an efficient furan ring-transfer reaction and a synthetic entry into the polycyclic ring systems

Yamaguchi, Yasuchika; Yamada, Hiromi; Hayakawa, Kenji; Kanematsu, Ken

doi:10.1021/jo00386a027

Cited by 42 publications

(2 citation statements)

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“…Six-membered-ring-forming intramolecular Diels-Alder reactions of isobenzofurans normally proceed with exo stereochemistry [50,[55][56][57][58]. Comparison of energies calculated using the PM3 semi-empirical single point molecular orbital method with 10 Â 10 configuration space for the most stable conformations (MM+ optimize followed by PM3 optimizations) of exo and endo Diels-Alder adducts reveals that the exo products are the most sta- ble products in both cases (Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of isoquinolines through the coupling of Fischer carbene complexes with o-alkynylpyridine carbonyl derivatives

Mukherjee

Jana

Ghorai

2009

Journal of Organometallic Chemistry

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Section: Resultsmentioning

confidence: 99%

Synthesis of isoquinolines through the coupling of Fischer carbene complexes with o-alkynylpyridine carbonyl derivatives

Mukherjee

Jana

Ghorai

2009

Journal of Organometallic Chemistry

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“…The alternative isomer is expected to exhibit nearly a 0 Hz coupling constant due to the nearly 90° dihedral angle. 5 This stereochemistry can result from protonation of the intermediate anion from the less hindered side prior to rearrangement of the resulting hexatriene ring system.…”

Section: Resultsmentioning

confidence: 99%

A novel stereoselective [8+2] double cycloaddition route to hydronaphthalene ring systems

Ying

Zhang

Wiget

et al. 2016

Tetrahedron Letters

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Substituted hydronaphthalenes where each of the ten carbons of the two-ring system contains functionality were obtained through a tandem [8+2] cycloaddition and base-catalyzed rearrangement process using dienylfurans and electron-deficient alkynes. If the [8+2] process is conducted under solvent-free conditions the process could be conducted in a single reaction flask without isolation of the chromatographically sensitive [8+2] cycloadducts. A mechanism involving base catalysed alkene positional isomerization followed by disrotatory electrocyclic ring closure was proposed for the key reaction step that converts [8+2] cycloadducts to hydronaphthalenes. The products undergo selective ring opening-isomerization processes upon treatment with Lewis acids.

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The Retro–Diels–Alder Reaction PartI.CCDienophiles

Rickborn

1998

Organic Reactions

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The Diels–Alder (“DA”) reaction is so familiar to organic chemists that the retro‐Diels–Alder or retro‐diene reaction (hereafter “rDA”) requires no conceptual introduction. However, a working definition is needed to indicate the coverage of this review. The intent is to include all reported examples of the general skeletal process excluded in this chapter. Any of the atoms in the starting material (cycloadduct) may be carbon or heteroatom, and substituents on all positions are allowed. In addition, any bond order available to the element in any oxidation state is included, as well as bonding to non‐nearest neighbor atoms (bicyclics, etc.). The volume of literature required separation of this review into two parts. Part I covers all expelled C–C dienophiles, i.e. those reactions that generate a new carbon‐carbon double or triple bond in the dienophile that is formed. Part II, to appear later, covers those expelled dienophiles in which one or both atoms is a heteroatom. Certain specific topics are intentionally omitted. These are: rDA reactions invoked under mass spectral conditions; rDA reactions of polymeric substrates; Electrocyclic processes, some of which are arguably very similar to rDA reactions (these are not addressed unless needed for clarification of an rDA sequence); and a thorough discussion of homo‐rDA reactions. CAS‐Online searches resulted in ca. 1,300 references, of which ca. 900 proved pertinent to the rDA topic as defined and delimited above. Active literature searching was halted in April 1995, but occasional more recent articles are included. Over 2,500 pertinent references were eventually found. Most were obtained by perusal of primary literature (articles) and secondary sources (books and reviews). Computer based search success was limited mainly by the failure of authors or abstractors to key‐word this topic, an especially common occurrence when the expelled dienophile was a simple substance such as N 2 or CO 2 . Overall, approximately 3,500 books, chapters, reviews, articles, and abstracts were consulted in an effort to make this review as comprehensive as possible. This was done with the certainty that some pertinent literature would be missed, tempered by the view that these omissions are probably also lost to any future rational search method. Many secondary sources proved valuable not only for in‐depth discussion of certain rDA reaction types, but also for providing comparisons with related topics. To assist the reader, these secondary sources are referenced (alphabetically by first author within broad subject areas) with a title or brief note on the topic(s) addressed. The first group lists earlier reviews with primary focus on rDA reactions, followed by items of Historical/General Interest, reviews that deal with Experimental Methods, DA reactions (general and specific), reviews of Related Topics (these impinge in more or less significant ways on rDA reactions), and general treatments of Theory and Mechanism.

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New generation and intramolecular Diels-Alder reaction of isobenzofurans: an efficient furan ring-transfer reaction and a synthetic entry into the polycyclic ring systems

Cited by 42 publications

References 0 publications

Synthesis of isoquinolines through the coupling of Fischer carbene complexes with o-alkynylpyridine carbonyl derivatives

Synthesis of isoquinolines through the coupling of Fischer carbene complexes with o-alkynylpyridine carbonyl derivatives

A novel stereoselective [8+2] double cycloaddition route to hydronaphthalene ring systems

The Retro–Diels–Alder Reaction PartI.CCDienophiles

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