Metal-free alkene carbooxygenation following tandem intramolecular alkoxylation/Claisen rearrangement: stereocontrolled access to bridged [4.2.1] lactones

Li, Long; Zhu, Xin‐Qi; Zhang, Yingqi; Bu, Hao‐Zhen; Yuan, Peng; Chen, Jinyu; Su, Jingyi; Deng, Xianming; Ye, Long‐Wu

doi:10.1039/c9sc00079h

Cited by 65 publications

(16 citation statements)

References 76 publications

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“…Brønsted acids are also very important catalytic species for Claisen rearrangement. Ye's group applied a simple and strong Brønsted acid, bistriflimide (HNTf 2 , (CF 3 SO 2 ) 2 NH, 1,1,1trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide) in the synthesis of bridged [4.2.1] lactones 74 (Scheme 15a) [42]. This reaction consisted of multiple steps, where the carbo-oxygenation of alkenes and Claisen rearrangement are considered as the main steps in constructing the bridged lactone moiety.…”

Section: Organocatalyzed Claisen Rearrangementmentioning

confidence: 99%

Recent Advances in Catalytic [3,3]-Sigmatropic Rearrangements

Lee

Kim

et al. 2022

Catalysts

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Carbon–carbon bond formation by [3,3]-sigmatropic rearrangement is a fundamental and powerful method that has been used to build organic molecules for a long time. Initially, Claisen and Cope rearrangements proceeded at high temperatures with limited scopes. By introducing catalytic systems, highly functionalized substrates have become accessible for forming complex structures under mild conditions, and asymmetric synthesis can be achieved by using chiral catalytic systems. This review describes recent breakthroughs in catalytic [3,3]-sigmatropic rearrangements since 2016. Detailed reaction mechanisms are discussed to enable an understanding of the reactivity and selectivity of the reactions. Finally, this review is inspires the development of new cascade reaction pathways employing catalytic [3,3]-sigmatropic rearrangement as related methodologies for the synthesis of complex functional molecules.

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Section: Organocatalyzed Claisen Rearrangementmentioning

confidence: 99%

Recent Advances in Catalytic [3,3]-Sigmatropic Rearrangements

Lee

Kim

et al. 2022

Catalysts

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“…Furthermore, the relevant intramolecular alkoxylation of ynamides initiated stereospecific Claisen rearrangement, and intramolecular hydroalkoxylation of ynamide-initiated stereospecific [1,3]-sigmatropic rearrangement was realized by our group by Brønsted acid catalysis, enabling practical and atom-economical assembly of a range of indole-fused bridged [4.2.1]lactones and another type of medium-sized lactams, respectively.…”

Section: Transition Metal-catalyzed Cycloisomerization-initiated Tand...mentioning

confidence: 99%

Transition Metal-Catalyzed Tandem Reactions of Ynamides for Divergent N-Heterocycle Synthesis

Hong

2020

Acc. Chem. Res.

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313

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“…A[ 3,3]-rearrangement and water trapping and sulfonamide expulsion results in the formation of indole fused lactone IV.B rønsted acid promoted lactone ring opening/CÀOb ond cleavage furnishes the cationic intermediate VI.I ntramolecular trapping of VI by electron-rich alkenyl group yields cationic intermediate VII which upon trapping by carboxylic group furnishes the final indole-fused [4.2.1] lactone 590.B iological evaluation of the indole-fused [4.2.1] lactones exhibitedt heir bioactivity against different breast cancerc ells, melanoma cells, and esophageal cancer cells( Scheme 149). [170]…”

Section: Metamorphosis Of Heteroarene-tethered Ynamidesmentioning

confidence: 99%

“…Biological evaluation of the indole‐fused [4.2.1] lactones exhibited their bioactivity against different breast cancer cells, melanoma cells, and esophageal cancer cells (Scheme 149). [170] …”

Section: Metamorphosis Of Heteroarene‐tethered Ynamidesmentioning

confidence: 99%

Heteroarene‐tethered Functionalized Alkyne Metamorphosis

Bag

Sawant

2020

Chemistry A European J

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Heteroarene-tethered functionalized alkynes are multipotents ynthons in organic chemistry.T his detailed Review described herein offers at horough discussion of the metamorphosis of heteroarene-tethered functionalized alkynes, an area which has earned much attention over the past decade in the straightforward synthesis of architecturally complex heterocyclics caffolds in atom and step economic manner.D epending upon the variety of functionalized al-kynes, this Review is divided into multiple sections. Amongst the vast array of synthetic transformations covered, dearomatizings pirocyclizations and cascades pirocyclization/rearrangementa re of great interest. Synthetic transformations involving the heteroarene-tethered functionalized alkynes with scope, challenges, limitations, mechanism, their application in the total synthesis of natural products and future perceptionsa re surveyed. [a] D. Bag, Prof.

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Metal-free alkene carbooxygenation following tandem intramolecular alkoxylation/Claisen rearrangement: stereocontrolled access to bridged [4.2.1] lactones

Abstract: A metal-free intramolecular tandem sequence involving alkoxylation, Claisen rearrangement and lactone expansion has been achieved.

Cited by 65 publications

References 76 publications

Recent Advances in Catalytic [3,3]-Sigmatropic Rearrangements

Recent Advances in Catalytic [3,3]-Sigmatropic Rearrangements

Transition Metal-Catalyzed Tandem Reactions of Ynamides for Divergent N-Heterocycle Synthesis

Heteroarene‐tethered Functionalized Alkyne Metamorphosis

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