Benzofulvenes in Trienamine Catalysis: Stereoselective Spiroindene Synthesis

Donslund, Bjarke S.; Nielsen, Rune Pagh; Mønsted, Sofie M. N.; Jørgensen, Karl Anker

doi:10.1002/ange.201605079

Cited by 12 publications

(2 citation statements)

References 59 publications

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“…Over the years, some synthetic methods have been developed and molecular functionalization studies have been carried out. Especially intramolecular cycloaddition or intermolecular cycloaddition reaction is mostly, such as intramolecular dearomatization cyclization of phenols [16], photo-induced intramolecular [2 + 2] cyclization [17], intermolecular [4 + 2] or [3 + 2] cycloaddition [18][19]. In addition, in order to further improve the reaction e ciency and enhance the diversity of product structures, transition metal catalysis and rearrangement reactions are also widely used in the synthesis of such products.…”

Section: Introductionmentioning

confidence: 99%

DFT study on the gold(I)-catalyzed cycloaddition and rearrangement reactions of allene-containing allylic silyl ether

Zhao¹,

Huo²,

Zhou³

2021

Preprint

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The DFT calculation of the B3LYP level was carried out to explore the reaction mechanism of the synthesis of spirocyclo[4, 5]decane skeleton by gold-catalyzed allenyl compounds. The more accurate energy under the CH3CN solvent in the experiment is calculated by the single point energy of the SMD model. Computational studies have shown that the reaction consists of three main steps: intramolecular cycloaddition of the end group carbon atoms of allenyl and vinyl groups, the semipinacol rearrangement process in which the four-membered ring is reconstructed into the five-membered ring, the elimination reaction releases the catalyst and obtains the product. The calculation results show that Zheng et al. reported that the gold-catalyzed synthesis reaction can easily occur under the experimental conditions due to its low activation free energy (12.42–16.79 kcal/mol). Furthermore, it was found that the MOMO(CH2)2 substituent has higher reactivity than the corresponding reactant of the phenyl substituent.

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Section: Introductionmentioning

confidence: 99%

DFT study on the gold(I)-catalyzed cycloaddition and rearrangement reactions of allene-containing allylic silyl ether

Zhao¹,

Huo²,

Zhou³

2021

Preprint

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“…of great interest, 1 arguably owing to their increasing presence in pharmaceutical applications, 2 molecular materials, 3 use as synthetic precursors, 4 and overall intriguing physical and chemical properties. In particular, the fulvene motif is a useful handle to probe aromaticity in what has been previously called an aromatic chameleon.…”

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confidence: 99%

A Simple and Mild Microwave-Based Synthesis of Novel Functionalized Benzofulvenes

Glass

Caspary

Fisher

et al. 2018

SynOpen

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Benzofulvenes and their derivatives are useful molecular entities having applications as biologically active molecules, polymer precursors, and optoelectronic devices. We have developed a simple and mild synthetic method for the formulation of a variety of these interesting compounds. Using carbonyl coupling techniques combined with microwave heating, a wide variety of functionalized benzofulvenes can be accessed rapidly in good yield. Furthermore, we have obtained five crystal structures further expanding a limited number of benzofulvene structures available.

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Asymmetric Intermolecular Rauhut−Currier Reaction for the Construction of 3,3‐Disubstituted Oxindoles with Quaternary Stereogenic Centers

Wang

Man

et al. 2017

Adv Synth Catal

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A remote cross Rauhut−Currier reaction utilizing vinyl ketones and para‐quinone methides derived from isatins was realized, which was successfully catalyzed using bifunctional phosphines, furnishing chiral 3,3‐disubstituted oxindoles in excellent enantioselectivities and high yields. The mechanistic studies demonstrated the key role of the alkyl hydrogen of the vinyl ketones, which conceivably interacted with the para‐quinone methide carbonyl group via the hydrogen bond, offering a new insight for the design of novel asymmetric reactions.magnified image

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Benzofulvenes in Trienamine Catalysis: Stereoselective Spiroindene Synthesis

Abstract: Scheme 4. Intramolecular cyclization reactions and crystal structures. Bn = benzyl, DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene;D MP = Dess-Martin periodinane. See the Supporting Information for further details.Angewandte Chemie Communications

Cited by 12 publications

References 59 publications

DFT study on the gold(I)-catalyzed cycloaddition and rearrangement reactions of allene-containing allylic silyl ether

DFT study on the gold(I)-catalyzed cycloaddition and rearrangement reactions of allene-containing allylic silyl ether

A Simple and Mild Microwave-Based Synthesis of Novel Functionalized Benzofulvenes

Asymmetric Intermolecular Rauhut−Currier Reaction for the Construction of 3,3‐Disubstituted Oxindoles with Quaternary Stereogenic Centers

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