A Dehydrogenative Diels–Alder Reaction of Prenyl Derivatives with 2,3‐Dichloro‐5,6‐dicyanobenzoquinone

Feng, Hong‐Xia; Wang, Yuan‐Yuan; Chen, Jie; Zhou, Ling

doi:10.1002/adsc.201401038

Cited by 25 publications

(16 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2015, Zhou and co-workers reported the DDQ-mediated dehydrogenative Diels-Alder reaction of prenyl derivatives (62 a)u nder metal-free conditions (Scheme 15). [42] The developed oxidative annulation reactiont olerated various prenyl derivatives in the presenceo ft he strong oxidant DDQ. Mechanistic studies indicated that the dehydrogenative Diels-Alder reaction proceeds through isoprene intermediate 64,w hich was generated through oxidation of prenyl derivative 62 a in the presence of DDQ, followed by cycloadditionw ith as econd equivalent of DDQ to form product 63 a.T ostress the synthetic value of the novel reaction, the authors demonstrated the reductiono ft he cycloaddition product to the more valuable 1,4dihydroxybenzene 64.…”

Section: Annulation Through Càcb Ond Formationmentioning

confidence: 99%

Sustainable, Oxidative, and Metal‐Free Annulation

Bering

Manna

Antonchick

2017

Chemistry A European J

View full text Add to dashboard Cite

Annulation has received steadily growing interest in the interplay with the increasing emphasis towards selective C-H bond functionalization reactions. Metal-free oxidative annulation through functionalization of inert and abundant C-H bonds offers great improvements in terms of atom- and step-economics as well as reduced waste production under mild reaction conditions. Annulation is considered to be a highly efficient strategy for the construction of cyclic molecules because at least two new bonds are formed within a single reaction step. The combination of annulation and direct C-H bond functionalization allows the efficient and straightforward synthesis of carbo- and heterocyclic molecules using simple and non-prefunctionalized precursors. This Concept highlights novel strategies and recent breakthroughs for metal-free annulation through C-H bond functionalization giving access to a variety of important structural motifs.

show abstract

Section: Annulation Through Càcb Ond Formationmentioning

confidence: 99%

Sustainable, Oxidative, and Metal‐Free Annulation

Bering

Manna

Antonchick

2017

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Zhou and co-workersd emonstrated an ice dehydrogenative Diels-Alder reaction of prenyl derivatives with DDQ, leading to as eries of cyclohexene derivatives with good to excellent yields and excellent diastereoselectivities (Scheme 34). [34] In this reaction, DDQ performs ad ual role:o xidanta nd dienophile.…”

Section: Scheme31 Formation Of Benzofulvene Through Ac Ascade Reactionmentioning

confidence: 99%

Recent Progress in Dehydro(genative) Diels–Alder Reaction

Zhou

Zhang

2015

Chemistry A European J

View full text Add to dashboard Cite

In recent years, remarkable progress has been made in dehydro or dehydrogenative Diels-Alder (D-A) reactions. This Minireview gives an overview of the major two strategies for dehydro(genative) Diels-Alder reactions, which differ in dehydrogenation and D-A cyclization sequence. Reactions in which D-A cycloaddition is followed by dehydrogenation are useful methods for the synthesis of various aromatic compounds, whereas advancements in dehydro genative procedures with oxidants or catalysts prior to D-A cycloaddition offer yet further new routes to functionalized cycloadducts. Recent leading findings are highlighted and the current state of the art, scope, and limitations of these processes are discussed in this Minireview.

show abstract

“…20 To the best of our knowledge, this represents the first example of isomerization of a vinyl p -QM to the corresponding diene; however, analogous formal dehydrogenation of prenylated derivatives to 1,3-butadienes has previously been reported. 21 …”

mentioning

confidence: 99%

Biomimetic Total Synthesis of (±)-Griffipavixanthone via a Cationic Cycloaddition–Cyclization Cascade

et al. 2017

View full text Add to dashboard Cite

We report the concise, biomimetic total synthesis of the dimeric, Diels–Alder natural product griffipavixanthone from a readily accessible prenylated xanthone monomer. The key step utilizes a novel intermolecular [4+2] cycloaddition–cyclization cascade between a vinyl p-quinone methide and an in situ generated isomeric diene promoted by either Lewis or Brønsted acids. Experimental and computational studies of the reaction pathway suggest that a stepwise, cationic Diels–Alder cycloaddition is operative.

show abstract

A Dehydrogenative Diels–Alder Reaction of Prenyl Derivatives with 2,3‐Dichloro‐5,6‐dicyanobenzoquinone

Abstract: An efficient dehydrogenative DielsAlder (DHDA) reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) has been developed under mild conditions, leading to a series of cyclohexene derivatives with good to excellent yields and excellent diastereoselectivity.

Cited by 25 publications

References 64 publications

Sustainable, Oxidative, and Metal‐Free Annulation

Sustainable, Oxidative, and Metal‐Free Annulation

Recent Progress in Dehydro(genative) Diels–Alder Reaction

Biomimetic Total Synthesis of (±)-Griffipavixanthone via a Cationic Cycloaddition–Cyclization Cascade

Contact Info

Product

Resources

About