Diastereo- and enantioselective palladium-catalyzed dearomative [4 + 2] cycloaddition of 3-nitroindoles

Suo, Jishuan; Du, Jiangfeng; Jiang, Yang-Jie; Chen, Di; Ding, Chang‐Hua; Hou, Xue‐Long

doi:10.1016/j.cclet.2019.04.028

Cited by 57 publications

(25 citation statements)

References 58 publications

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“… Palladium‐catalyzed asymmetric [4+2] cycloadditions of 4‐vinyl benzoxazinones with 3‐nitroindoles [43] …”

Section: π‐Allyl Palladium Bearing N‐nucleophilementioning

confidence: 99%

“…In 2019, Hou, Ding and coworkers reported the asymmetric decaboxylative [4 + 2] cycloaddition of 108 with 3-nitroindoles 122 (Scheme 59). [43] The reaction includes a dearomative process of 3-nitroindoles, which is usually not easy. This reaction was fastidious for the ligand.…”

Section: Decarboxylative [4 + 2] Cycloadditions Of 4-vinyl Benzoxazin...mentioning

confidence: 99%

“…Palladium-catalyzed asymmetric [4 + 2] cycloadditions of 4-vinyl benzoxazinones with 3-nitroindoles. [43] between N-H and enolate-oxygen might be the dominating factor for N-H substrate (3.2L).…”

Section: Decarboxylative [4 + 2] Cycloadditions Of 4-vinyl Benzoxazin...mentioning

confidence: 99%

See 2 more Smart Citations

Advances in Palladium‐Catalyzed Decarboxylative Cycloadditions of Cyclic Carbonates, Carbamates and Lactones

You

Zhang

et al. 2022

ChemCatChem

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Palladium‐catalyzed decarboxylative cycloadditions have emerged as highly effective methods for constructing structurally diverse carbo‐ and heterocycles because of the formation of at least two carbon‐carbon or carbon‐heteroatom bonds in a single step. It is of great interest to chemists that this type of cycloaddition reactions possesses some special advantages such as high reactivity, exclusive regioselectivity, and good functional group compatibility. Based on these qualities, palladium‐catalyzed decarboxylative cycloadditions present strong ability in synthetic chemistry and have been flourished especially in the last five years. In this review, the achievements in palladium‐catalyzed decarboxylative cycloadditions involving cyclic carbonates, carbamates, and lactones for accessing oxacyclo‐, azacyclo‐ and carbocyclic compounds are addressed. Mechanistic insights and some synthetic applications toward the synthesis of natural products are discussed. The challenges and opportunities of this field are also outlined.

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“… Palladium‐catalyzed asymmetric [4+2] cycloadditions of 4‐vinyl benzoxazinones with 3‐nitroindoles [43] …”

Section: π‐Allyl Palladium Bearing N‐nucleophilementioning

confidence: 99%

Section: Decarboxylative [4 + 2] Cycloadditions Of 4-vinyl Benzoxazin...mentioning

confidence: 99%

See 1 more Smart Citation

Advances in Palladium‐Catalyzed Decarboxylative Cycloadditions of Cyclic Carbonates, Carbamates and Lactones

You

Zhang

et al. 2022

ChemCatChem

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“…Their mechanistic proposal starts with a reaction between enal 69 and the NHC precursor catalyst In a related study, Hou and co-workers further expanded the scope of nucleophiles and showed that vinyl benzoxazinanone derivatives served as the formal four-membered 1,4dipole counterparts (Scheme 13A). [22] In the presence of catalytic amounts of Pd 2 (dba) 3 •CHCl 3 and chiral SIOCPhox type ligand 76, vinyl benzoxazinanones 75 efficiently reacted with 3-nitroindoles 74 through a dearomatization approach, affording a series of chiral tetrahydroindoloquinoline frameworks 77 in high yields and with excellent diastereo-and enantioselectivities. It is worth noting that no cycloaddition product was detected when tosyl group on the vinyl benzoxazinanone was replaced with proton, nosyl, or acetyl.…”

Section: Nitro(hetero)arenes As the Michael Acceptors Via Annulationmentioning

confidence: 99%

Dearomatization of Nitro(hetero)arenes through Annulation

Wang

Ren

2022

Eur J Org Chem

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Dearomatization reactions employing simple aromatic compounds have showcased remarkable progress in the recent decade and have emerged as one of the most straightforward and powerful tools for the creation of highly functionalized, three-dimensional molecular frameworks commonly encountered in medicinal chemistry and life sciences. Among the aromatic compounds in use, nitro(hetero)arenes, which feature a less pronounced aromatic character due to the presence of highly electron-withdrawing nitro group, have been extensively used in different types of dearomatization reactions. The dearomative annulation reaction serves as a powerful and versatile method for the construction of complex polycyclic systems. This overview presents a brief summary of recent impressive advances in nitro(hetero)arenes dearomative annulation and provides some inspirations for future research.

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“…( S c , R phos ,R a )‐SIOCPhox L7 proved to be viable ligand to deliver excellent enantioselectivity (Table 6). [38] The N ‐protecting group of 3‐nitroindole 27 and vinyl benzoxazinanone 32 had a significant influence on the cycloaddition. N ‐Ac‐3‐nitroindole proved to be unreactive while N ‐Boc and N ‐Ts‐3‐nitroindoles 27 gave high yield and stereoselectivity.…”

Section: Palladium‐catalyzed Asymmetric Cycloadditions Of Activated Alkenesmentioning

confidence: 99%

Development of Dipolarophiles for Catalytic Asymmetric Cycloadditions through Pd‐π‐Allyl Zwitterions

Yang

Ding

et al. 2021

The Chemical Record

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The development of new and efficient methodology for the construction of optically active molecules is of great interest in both synthetic organic and medicinal chemistry fields. To this end, the personal account summarizes our studies on the development of electron‐deficient alkenes, allenes, and alkynes containing single activator as new dipolarophiles for Pd‐catalyzed asymmetric cycloaddition reactions. These new dipolarophiles can participate in Pd‐catalyzed asymmetric [3+2] and [4+2] cycloadditions through Pd‐π‐allyl 1,3‐ and 1,4‐zwitterions in‐situ generated by the reaction of Pd(0) catalyst with vinyl aziridines, vinyl epoxides, vinyl cyclopropanes, 4‐vinyl‐1,3‐dioxan‐2‐ones, and vinyl benzoxazinanones. These [3+2] and [4+2] cycloadditions provide efficient approaches to a wide range of enantiomerically enriched five‐ and six‐membered ring compounds containing contiguous chiral centers with high to excellent chemo‐, diastereo‐, and enantioselectivities. The utilities of these protocols are demonstrated by transformation of the cycloadducts into other useful chiral building blocks. DFT calculations reveal the dissimilar reactivity of different electron deficient alkenes and rationalize the mechanism and stereo‐control of the reaction. A Pd‐catalyzed inverse [3+2] cycloaddition is disclosed.

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Diastereo- and enantioselective palladium-catalyzed dearomative [4 + 2] cycloaddition of 3-nitroindoles

Cited by 57 publications

References 58 publications

Advances in Palladium‐Catalyzed Decarboxylative Cycloadditions of Cyclic Carbonates, Carbamates and Lactones

Advances in Palladium‐Catalyzed Decarboxylative Cycloadditions of Cyclic Carbonates, Carbamates and Lactones

Dearomatization of Nitro(hetero)arenes through Annulation

Development of Dipolarophiles for Catalytic Asymmetric Cycloadditions through Pd‐π‐Allyl Zwitterions

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