Palladium-catalyzed stereoselective intramolecular cyclization and Suzuki coupling of N -arylsulfonyl-α-chloroenamides promoted by a γ-hydroxy group

Yabuuchi, Yuto; Sakamoto, Kenta; Yoshimura, Tetsuzo; Matsuo, Jun‐ichi

doi:10.1016/j.tet.2018.06.010

Cited by 5 publications

(2 citation statements)

References 27 publications

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“…Matsuo and co-workers 40 reported, in 2018, the palladium-catalyzed stereoselective intramolecular cyclization of N -arylsulfonyl-α-chloroenamides promoted by a γ-hydroxy group. They showed that both E - and Z -isomers reacted stereoselectively to give the corresponding ( E )-2,3-dihydrobenzoisothiazole 1,1-dioxides (Scheme 58 ).…”

Section: Transformations Of α-Haloenamidesmentioning

confidence: 99%

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α-Haloenamides: Synthesis and Subsequent Transformations

Feray¹,

Bertrand²,

galibert³

2022

Synthesis

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Section: Transformations Of α-Haloenamidesmentioning

confidence: 99%

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confidence: 99%

α-Haloenamides: Synthesis and Subsequent Transformations

Feray¹,

Bertrand²,

galibert³

2022

Synthesis

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Suzuki–Miyaura Cross‐Coupling

Pagett

Lloyd‐Jones

2019

Organic Reactions

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The Suzuki–Miyaura cross coupling reaction uses a metal catalyst to create carbon–carbon bonds from organoboron reagents and organo(pseudo)halides. By careful adjustment of the ligand system, solvents, and other additives, this reaction can couple a diverse range of sp‐, sp 2 ‐, and sp 3 ‐hybridized organoboron and organo(pseudo)halide reactants. The Suzuki–Miyaura cross coupling reaction has become preeminent in both small‐ and large‐scale synthesis owing to its mild reaction conditions, predictable stereochemical outcomes, chemoselectivity, functional‐group compatibility, and use of relatively non‐toxic and air‐stable starting materials. This chapter describes the theoretical and practical aspects of the palladium‐catalyzed Suzuki–Miyaura cross‐coupling reaction. A broad overview of the reaction mechanism and scope is described, with selected examples of how mechanistic insights have enabled progress in the development of this coupling reaction. Examples include early reaction discovery as well as modern applications in synthesis using a diverse array of organoboron and organo(pseudo)halide reactants, and on scales that range from milligram to multi‐kilogram. Tabular surveys are organized by the structure of the transferable group attached to boron as the primary rubric (alkyl, alkenyl, aryl, alkynyl, then heterocyclic), with the structure of the electrophile as the secondary rubric. Selected literature is covered from the seminal paper in 1979 to mid‐2018.

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DABCO-Catalyzed Michael/Alkylation Cascade Reactions Involving α-Substituted Ammonium Ylides for the Construction of Spirocyclopropyl Oxindoles: Access to the Powerful Chemical Leads against HIV-1

Chen

2020

J. Org. Chem.

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A novel Michael/alkylation cascade reaction of Nunprotected 3-bromooxindoles with α,β-unsaturated acyl phosphonates using DABCO as a robust catalyst followed by the derivatization of the acyl phosphonate intermediates in situ has been developed. This scenario enables rapid access to a diverse set of highly functionalized spirocyclopropyl oxindoles in moderate yields with good to excellent diastereoselectivities, which are analogues of a high active non-nucleoside reverse transcriptase inhibitor against HIV-1. The synthetic potential of this tactic has been highlighted by a gram-scale reaction and Suzuki crosscoupling reactions of the product. Moreover, the reaction mechanism has been tentatively elucidated by control experiments and dynamic high-resolution mass spectrometry studies, which indicates that the Michael/alkylation cascade reaction involves DABCO-derived α-substituted ammonium ylides.

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Palladium-catalyzed stereoselective intramolecular cyclization and Suzuki coupling of N -arylsulfonyl-α-chloroenamides promoted by a γ-hydroxy group

Cited by 5 publications

References 27 publications

α-Haloenamides: Synthesis and Subsequent Transformations

α-Haloenamides: Synthesis and Subsequent Transformations

Suzuki–Miyaura Cross‐Coupling

DABCO-Catalyzed Michael/Alkylation Cascade Reactions Involving α-Substituted Ammonium Ylides for the Construction of Spirocyclopropyl Oxindoles: Access to the Powerful Chemical Leads against HIV-1

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