XtalFluor-E® mediated proto-functionalization of N-vinyl amides: access to N-acetyl N,O-acetals

Yi, Yong; Gholami, Hadi; Morrow, Mark; Borhan, Babak

doi:10.1039/c7ob02283b

Cited by 13 publications

(14 citation statements)

References 31 publications

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Section: Synthetic Methods For Preparing N -Acyl- N O -Acetalsmentioning

confidence: 99%

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Progress in the Synthesis of N-Acyl-N,O-acetals

Shao

et al. 2021

Synthesis

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N-Acyl-N,O-acetals are key component a variety of bioactive natural products. Furthermore， they are synthetic equivalents of unstable N-acylimines and building blocks in organic synthesis. Tremendous efforts have been made to the synthesis of such acetals, these methods can roughly be classified into two categories: electrochemical oxidation and chemical methods. Herein, we want to summarize the progress made on the preparation of the subunits, which may provide assistance for the development of new synthetic methods of N-acyl-N,O-acetals.

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Section: Synthetic Methods For Preparing N -Acyl- N O -Acetalsmentioning

confidence: 99%

“…By utilizing this reaction, a wide range of N-acyl-N,O-or -N,S-acetals 85 were produced in nearly quantitative yields from various types of enamide substrates 84 (Scheme 34). 39 Scheme 31 Ti(OEt) 4 -mediated construction of N-acyl-N,O-acetals. a Yield of N-acyl-N,O-acetal when Sc(OTf) 3 was used as catalyst.…”

Section: Short Review Synthesismentioning

confidence: 99%

Progress in the Synthesis of N-Acyl-N,O-acetals

Shao

et al. 2021

Synthesis

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“…IR (ATR, ν in cm –1 ): 3227 (w), 2935 (w), 1635 (s), 1605 (m), 1579 (m), 1540 (s), 1489 (m), 1470 (m), 1445 (m), 1364 (w), 1320 (m), 1298 (m), 1260 (m), 1198 (m), 1143 (m), 1096 (s), 1047 (m), 1027 (m), 1014 (m), 939 (m), 920 (m), 842 (m), 808 (m), 765 (w), 707 (s), 693 (s), 666 (m). Analytical data match those reported in the literature …”

Section: Methodsmentioning

confidence: 99%

“…Analytical data match those reported in the literature. 35 Synthesis of N-(1-Methoxy-2-tosylpropyl)benzamide 4a from Lithium Sulfinate 9a. A solution of 1-iodo-4-methylbenzene 8a (1.6 g, 7.5 mmol, 1.0 equiv) in Et 2 O (15 mL) was treated with nBuLi (2.9 mL, 2.58 M in hexane, 7.5 mmol, 1.0 equiv) dropwise at 0 °C (ice bath cooling).…”

mentioning

confidence: 99%

Iron(III)-Mediated Oxysulfonylation of Enamides with Sodium and Lithium Sulfinates

et al. 2020

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An iron-mediated vicinal difunctionalization of enamides and enecarbamates with sulfinic acid salts and alcohols is described. This reaction proceeds under mild conditions and furnishes the oxysulfonylated products in moderate to excellent yields. Moreover, the direct incorporation of sulfur dioxide into the sulfonylated products via organolithium chemistry has been achieved. The formed NO -acetals are competent acylimine precursors. Their utilization as building block for the synthesis of biologically relevant β-amidosulfones is described as well. Introduction: Molecules bearing sulfonyl-derived functional groups, such as sulfones or sulfonamides, play an important role in organic chemistry and are widely used in various fields. 1,2 Among the different classes of sulfonyl-derived functional groups, sulfones are of particular interest. They display intriguing chemical and physical properties as well as interesting biological activities. Sulfones, which are often considered as chemical chameleons 3 , are versatile building blocks in organic synthesis. The sulfone motif can be found in various molecules with different applications ranging from agrochemcials and functional materials to active pharmaceutical ingredients. 2-4 Traditional approaches for the construction of sulfones include Friedel-Crafts type reactions of arenes with sulfonyl chlorides 5 , the oxidation of sulfides and sulfoxides 6 , addition reactions of sulfonyl radicals to alkenes and alkynes 7 or the electrophilic trapping of sulfinic acid salts 8,9. In the last ten years novel approaches based on the direct incorporation of sulfur dioxide 10, 11 or the functionalization of C-H bonds 12,13 have emerged as attractive and more sustainable alternatives.

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“…13 9, 133.0, 132.5, 128.9, 127.3, 80.8, 60.8, 56.3, 44.4, Analytical data match those reported in the literature. 34 Synthesis of compound 4a from lithium sulfinate 9a: A solution of 1-iodo-4-methylbenzene 8a (1.6 g, 7.5 mmol, 1.0 equiv) in Et2O (15 mL) was treated with nBuLi (2.9 mL, 2.58 M in hexane, 7.5 mmol, 1.0 equiv) dropwise at 0 °C (ice bath cooling). The mixture was allowed to stir at 0 °C for 30 min.…”

Section: Synthesis Of Compoundmentioning

confidence: 99%

Iron(III)-Mediated Oxy-Sulfonylation of Enamides with Sodium and Lithium Sulfinates

Kramer¹,

Halaczkiewicz²,

Sun³

et al. 2019

Preprint

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An iron-mediated vicinal difunctionalization of enamides and enecarbamates with sulfinic acid salts and alcohols is described. This reaction proceeds under mild conditions and furnishes the oxy-sulfonylated products in moderate to excellent yields. Moreover, the direct incorporation of sulfur dioxide into the sulfonylated products via organolithium chemistry has been achieved. The formed N-O-acetals are competent acylimine precursors. Their utilization as building block for the synthesis of biologically relevant β-amidosulfones is described as well.

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XtalFluor-E® mediated proto-functionalization of N-vinyl amides: access to N-acetyl N,O-acetals

Cited by 13 publications

References 31 publications

Progress in the Synthesis of N-Acyl-N,O-acetals

Progress in the Synthesis of N-Acyl-N,O-acetals

Iron(III)-Mediated Oxysulfonylation of Enamides with Sodium and Lithium Sulfinates

Iron(III)-Mediated Oxy-Sulfonylation of Enamides with Sodium and Lithium Sulfinates

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