Asymmetric Dearomatizative Diels–Alder Reaction for the Construction of Hydrodibenzo[<i>b</i>,<i>d</i>]furan Frameworks with Tetrasubstituted Stereogenic Centers

Xiao, Ben‐Xian; Du, Wei; Chen, Ying‐Chun

doi:10.1002/adsc.201601207

Cited by 43 publications

(10 citation statements)

References 97 publications

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“…[56][57][58] Here, we report a highly stereoselective palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes. 53,[59][60][61][62][63][64]…”

Section: The Bigger Picturementioning

confidence: 99%

Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans

Cheng

Zhang

Yue

et al. 2017

Chem

184

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Stereoselective construction of highly functionalized heterocyclic molecules is an ongoing concern for the chemical community. Among the various strategies developed with this goal, catalytic asymmetric dearomatization, an attractive method for constucting cyclic molecules with multiple stereocenters from readily available aromatic compounds, has received extensive attention in recent years. Here, we report a highly stereoselective construction of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes via palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes, respectively. Good to excellent yields (63%-92%), diastereoselectivity (13/1 / >20/1 dr), and enantioselectivity (75%-95% ee) were obtained, leading to products with vicinal stereogenic carbon centers. The reaction features wide substrate scope and diverse transformations of the products.

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“…[56][57][58] Here, we report a highly stereoselective palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes. 53,[59][60][61][62][63][64]…”

Section: The Bigger Picturementioning

confidence: 99%

Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans

Cheng

Zhang

Yue

et al. 2017

Chem

184

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“…The synthesized products 7-E and 7-OH represents the framework of galantamine natural product. [6b] In 2017, Chen and co-workers developed [7] a chiral primary amine 8 catalyzed asymmetric [4 + 2] cycloaddition strategy for the synthesis of tetrahydrodibenzo[b,d]furans 9 from 2-(3-vinylbenzofuran-2-yl)ethan-1-ones 10 and 3-olefinic-7-azaoxindoles 11 via dearomatization of benzofuran ring (Scheme 2A). The proposed transition state 12 (Scheme 2B) proceeds via an exoselective [4 + 2] cycloaddition and confirmed from X-ray crystallographic analysis.…”

Section: The [4 + 2] Cycloaddition Reactionsmentioning

confidence: 99%

Recent Dearomatization Strategies of Benzofurans and Benzothiophenes

Nair

Baire

2021

Asian J Org Chem

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This review article discusses about the recent developments in the area of the strategies for the dearomatization of benzofurans and benzothiophenes (2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). The readers can understand the current state of art of this intriguingly important area in organic synthesis for the generation of diversely functionalized molecules, polycyclic systems from highly abundant benzofurans and benzothiophenes. We hope that the current review article would help the synthetic community for the design and development of new strategies as well as further growth of this novel and rapidly growing area of research.

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“…The 3,5‐dienone type substrate easily condensed with Cinchona alkaloid ‐ derived primary amine catalyst Cat.19 and in situ formed trienamine intermediate by transient dearomatization. Thereafter, a [4+2] cycloaddition to construct spirocyclic frameworks 129 with fair to good yields and good to excellent enantioselectivities (Scheme ) …”

Section: Dienals and Dienones In Trienamine Catalysismentioning

confidence: 99%

Polyenals and Polyenones in Aminocatalysis: A Decade Building Complex Frameworks from Simple Blocks

et al. 2020

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Polyenals and polyenones are simple chemical compounds which can be constructed into large and complex structures by virtue of aminocatalysis. In the past eight years, new aminocatalytic activation modes based on trienamine, cross-trienamine, tetraenamine, iminium ion, and vinylogous iminium ion intermediates have attracted great attention in the field of asymmetric synthesis. Key to the increasing focus is their inherent ability to allow functionalization of remote sites with excel-[a] Dr.

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Asymmetric Dearomatizative Diels–Alder Reaction for the Construction of Hydrodibenzo[b,d]furan Frameworks with Tetrasubstituted Stereogenic Centers

Cited by 43 publications

References 97 publications

Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans

Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans

Recent Dearomatization Strategies of Benzofurans and Benzothiophenes

Polyenals and Polyenones in Aminocatalysis: A Decade Building Complex Frameworks from Simple Blocks

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