Azadiene Diels−Alder Cycloaddition of Fulvenes:  A Facile Approach to the [1]Pyrindine System

Hong, Bor‐Cherng; Wu, Jian‐Lin; Gupta, Arun Kumar; Hallur, Mahanandeesha Siddappa; Liao, Ju‐Hsiou

doi:10.1021/ol048762c

Cited by 37 publications

(13 citation statements)

References 29 publications

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“…Pentafulvenes show dual capabilities in DACs, with documented examples of them functioning as both dienes and dienophiles [55,114,150–151 154,159,174–176 227–229]. The exact nature of the fulvene moiety is dependent mostly on its substituents (e.g., EWG or EDG) relative to the other reactants [6,42,45,67,103,153,230].…”

Section: Reviewmentioning

confidence: 99%

“…Conversely, when the fulvene has an EWG attached, it is more likely to function as a dienophile in an inverse electron-demand Diels–Alder (iEDDA) reaction [153–154 156]. This requires the other reactant to have strong EDGs in order to function as a diene, otherwise fulvene dimerization becomes the preferred reaction, causing the formation of complex products.…”

Section: Reviewmentioning

confidence: 99%

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An overview of the cycloaddition chemistry of fulvenes and emerging applications

Swan¹,

Platts²,

Blencowe³

2019

Beilstein J. Org. Chem.

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The unusual electronic properties and unique reactivity of fulvenes have interested researchers for over a century. The propensity to form dipolar structures at relatively low temperatures and to participate as various components in cycloaddition reactions, often highly selectively, makes them ideal for the synthesis of complex polycyclic carbon scaffolds. As a result, fulvene cycloaddition chemistry has been employed extensively for the synthesis of natural products. More recently, fulvene cycloaddition chemistry has also found application to other areas including materials chemistry and dynamic combinatorial chemistry. This highlight article discusses the unusual properties of fulvenes and their varied cycloaddition chemistry, focussing on applications in organic and natural synthesis, dynamic combinatorial chemistry and materials chemistry, including dynamers, hydrogels and charge transfer complexes. Tables providing comprehensive directories of fulvene cycloaddition chemistry are provided, including fulvene intramolecular and intermolecular cycloadditions complete with reactant partners and their resulting cyclic adducts, which provide a useful reference source for synthetic chemists working with fulvenes and complex polycyclic scaffolds.

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Section: Reviewmentioning

confidence: 99%

Section: Reviewmentioning

confidence: 99%

An overview of the cycloaddition chemistry of fulvenes and emerging applications

Swan¹,

Platts²,

Blencowe³

2019

Beilstein J. Org. Chem.

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“…The synthetic relevance of this methodology has been demonstrated by its utility in the synthesis of various oxabridged cycloheptanoid fragments of complex natural products, [58] such as phorbol having antitumor and anti-HIV activity, [59] the antibiotic guanacastepene, [60] phomoidride B, [61] and a cyathin diterpene. [62] A more recent application of this methodology was described by Wender et al who developed a general route to the BC-ring system of 12-hydroxydaphnetoxins, which are members of the structurally fascinating daphnane diterpene family, exhibiting a wide range of significant biological activities.…”

Section: Intramolecular [5 + 2] Cycloadditions Of Oxidopyrylium Ionsmentioning

confidence: 99%

“…and Radhakrishnan 4. The synthetic relevance of this methodology has been demonstrated by its utility in the synthesis of various oxabridged cycloheptanoid fragments of complex natural products,58 such as phorbol having antitumor and anti‐HIV activity,59 the antibiotic guanacastepene,60 phomoidride B,61 and a cyathin diterpene 62. A more recent application of this methodology was described by Wender et al.…”

Section: [5+2] Cycloadditions Of Oxidopyrylium Ionsmentioning

confidence: 99%

Recent Developments in the [5+2] Cycloaddition

Pellissier¹

2011

Adv Synth Catal

207

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The rapid generation of molecular complexity in a relatively easy manner has made the [5 + 2] cycloaddition approach a highly useful tool in the synthesis of a wide number of complex natural products and important biologically active products containing seven-membered rings. Besides the common and highly efficient [5 + 2] cycloadditions of oxidopyrylium and oxidopyridinium ions with p-systems which offer an easy access to a wide range of novel heterocyclic seven-membered ring molecules with a oxygen or nitrogen bridge, and the less employed [5 + 2] photocycloadditions, the metal-catalyzed [5 + 2] cycloadditions have attracted a lot of attention and have become one of the most popular ways of constructing seven-membered ring products. All these cycloadducts can be synthetically manipulated easily toward a number of interesting molecular structures with high potential applications.

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“…In cycloadditions, pentafulvenes can participate as a 2π, 4π or 6π component and have served as excellent synthons for the synthesis of triquinanes, pyrindines etc. [16] Investigations from our own laboratory [17] have unraveled the interesting reactivity profile of fulvenes in cycloaddition reactions. Fulvenes have found extensive use as key intermediates in the synthesis of natural products such as hirsutene, [18] capnellene, [19] β-vetivone, [20] hinesol, [21] and silphinene.…”

Section: Introductionmentioning

confidence: 99%

A Simple and Efficient Strategy Towards Eleven‐Membered Carbocycles via Novel Synthetic Transformations of Pentafulvenes

et al. 2007

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A novel and versatile method towards the synthesis of eleven-membered carbocycles through a three step reaction sequence from pentafulvenes is described. The [6+3] adduct of pentafulvenes with 3-oxidopyrylium betaine on selective reduction followed by ruthenium catalyzed oxidative cleavage afforded a novel eleven-membered carbocyclic triketone with a bridging ether linkage. The methodology described

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Azadiene Diels−Alder Cycloaddition of Fulvenes: A Facile Approach to the [1]Pyrindine System

Abstract: [reaction: see text] Regioselective and stereoselective inverse-electron-demand Diels-Alder reaction of N-sulfonyl-1-aza-1,3-butadiene with fulvenes are described. The methodology provides an efficient and novel route to tetrahydro-[1]pyrindine systems.

Cited by 37 publications

References 29 publications

An overview of the cycloaddition chemistry of fulvenes and emerging applications

An overview of the cycloaddition chemistry of fulvenes and emerging applications

Recent Developments in the [5+2] Cycloaddition

A Simple and Efficient Strategy Towards Eleven‐Membered Carbocycles via Novel Synthetic Transformations of Pentafulvenes

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