Heteroannulation of Arynes with α‐Amino Imides: Synthesis of 2,2‐Disubstituted Indolin‐3‐ones and Application to the Enantioselective Total Synthesis of (+)‐Hinckdentine A

Torres‐Ochoa, Rubén O.; Buyck, Thomas; Wang, Qian; Zhu, Jieping

doi:10.1002/anie.201800746

Cited by 62 publications

(27 citation statements)

References 56 publications

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“…The catalytic asymmetric Michael addition of methyl α-(2-nitrophenyl)-α-isocyano acetate to phenyl vinyl selenone in the presence of a quinidine-derived bifunctional catalyst was the key step for the enantioselective construction of the (+)-Hinckdentine A (Scheme 23). This is a marine alkaloid isolated from the bryozoan Hincksinoflustra denticulata collected from Tasmania's eastern coast [55]. In 2014, Zhu reported the reactions of 2-substituted isocyanoacetates, alkenyl selenones and water to afford 4,4-disubstituted 1,3-oxazinan-2-ones in good to excellent yields [56].…”

Section: Enantioselective Organocatalytic Transformationsmentioning

confidence: 99%

Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones

et al. 2021

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Section: Enantioselective Organocatalytic Transformationsmentioning

confidence: 99%

Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones

et al. 2021

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“…In addition to alkylation by alkyl halides, pyrrolidones and caprolactams can be N-acylated (320)(321)(322)(323)(324) or N-alkoxycarbonylated (producing carbamate esters) (325-329) by reaction with the appropriate acid anhydride, acyl halide, dialkyl dicarbonate, or chloroformate (Scheme 6).…”

Section: N-alkylation Acylation and Arylation Of Pyrrolidones And Cap...mentioning

confidence: 99%

Introduction to Pyrrolidone and Caprolactam Chemistry

Chenault

2021

Handbook of Pyrrolidone and Caprolactam Based Materials

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Pyrrolidones and caprolactams are important structural components of solvents, surfactants, polymers, natural products, and pharmaceuticals. This chapter provides an introduction to the structure, conformation, physical properties and reactivity of pyrrolidones and caprolactams. It begins with an overview of the nomenclature of lactams since there are several systems of nomenclature in practice, plus common names and various syncretisms. Next, the structures of pyrrolidone and caprolactam are discussed, starting with the X-ray crystal structures of pyrrolidone, N-methylpyrrolidone (NMP) and caprolactam. The conformational flexibility and ring strain of the two ring systems are also covered.Physical properties, such as dipole moments, the enthalpies of formation, vaporization and fusion, boiling points and melting points, are described. An attempt is made to put the properties of pyrrolidones and caprolactams into context with those of other lactams, amides and even lactones and cyclic ketones. Brønsted and Lewis basicity, acidity, hydrogen bonding and solubility are covered.Finally, a brief description of the basic reactivity of pyrrolidones and caprolactams is given. Topics covered are N-, O-, and α-C-alkylation, hydrolysis, reactions with organometallics, reduction, oxidation, and ring-opening polymerization. The intent is to give a concise physical organic perspective on reactivity (and stability) more than an extended treatise on synthetic elaborations. Definition and Nomenclature of LactamsLactams are cyclic amides in which both the carbonyl carbon and nitrogen atom of the amide group are part of a ring. The name, lactam, is a portmanteau of lactone (cyclic ester) and amide.Nomenclature of lactams follows a variety of conventions (Figure 1 and Table 1). The International Union of Pure and Applied Chemistry (IUPAC) recommends naming lactams as heterocyclic pseudoketones (IUPAC method 1) or by substituting lactam for the

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“…Zhu and coworkers disclosed a novel heteroannulation of arynes using a-amino imides. 94 This method was employed for the total synthesis of (+)hinckdentine A (48, Scheme 16). Recently, our lab reported the non-biomimetic total syntheses of (-)jorunnamycin A (50, Scheme 17) and (-)-jorumycin in 15 and 16 steps, respectively.…”

Section: Scheme 15 Sarpong's Acyl-alkylation Approach To the Centralmentioning

confidence: 99%

Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-acetylphenyl)acetate

Wright¹

2019

Org. Synth.

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Heteroannulation of Arynes with α‐Amino Imides: Synthesis of 2,2‐Disubstituted Indolin‐3‐ones and Application to the Enantioselective Total Synthesis of (+)‐Hinckdentine A

Cited by 62 publications

References 56 publications

Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones

Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones

Introduction to Pyrrolidone and Caprolactam Chemistry

Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-acetylphenyl)acetate

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