A Novel Synthesis of (<i>E</i>)‐2‐Alkenylborane from Chiral Borane and Diazoalkene: Asymmetric Alkenylboration of Aldehydes

Pak, Gyungah; Kim, Jimin

doi:10.1002/bkcs.11909

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2021

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Cited by 2 publications

(1 citation statement)

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“…Diazo compounds are employed as appealing synthetic substrates for building complex organic molecules 17 . Recently, we have utilized diazo compounds as the reacting partners with vinyl ethers, 18a β‐enamino esters 18b or 1,3‐diketo esters 18c for the synthesis of 4‐pyrones.…”

Section: Introductionmentioning

confidence: 99%

In(III)‐Catalyzed O‐Annulation of Cyclic Diazodicarbonyls with 2‐Naphthol, 6‐Quinolinol, β‐Tetralone, and 9‐Phenanthrol to Access Diverse Benzochromones

Maezono

Khanal

Chaudhary

et al. 2021

Bulletin Korean Chem Soc

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In(III)‐Catalyzed O‐annulation of cyclic diazodicarbonyl compounds with 2‐naphthols, 6‐quinolinol, β‐tetralone, and 9‐phenanthrol is developed. This novel synthetic strategy paves a facile and desired access to diverse and functionalized benzochromones. This imperative protocol involves domino carbene generation, ketene formation through Wolff‐rearrangement, nucleophilic addition, H‐migration, intramolecular cyclization, and elimination of water.

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Section: Introductionmentioning

confidence: 99%

In(III)‐Catalyzed O‐Annulation of Cyclic Diazodicarbonyls with 2‐Naphthol, 6‐Quinolinol, β‐Tetralone, and 9‐Phenanthrol to Access Diverse Benzochromones

Maezono

Khanal

Chaudhary

et al. 2021

Bulletin Korean Chem Soc

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Visible‐Light Photoredox‐Catalyzed α‐Allylation of α‐Bromocarbonyl Compounds Using Allyltrimethylsilane

Gontala

Jang

Woo

2021

Bulletin Korean Chem Soc

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The development of a greener allylation reagent for α‐allylation of carbonyl compounds is of great necessity. Here we present allyltrimethylsilane as a novel allylation reagent in the photoredox‐catalyzed α‐allylation of carbonyl compounds such as ketones, esters, and amides. The reaction process shows good functional group tolerance and generates a good yield of the product. The reaction mechanism is a radical‐mediated reaction by photo‐induced single electron transfer.

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A Novel Synthesis of (E)‐2‐Alkenylborane from Chiral Borane and Diazoalkene: Asymmetric Alkenylboration of Aldehydes

Cited by 2 publications

References 15 publications

In(III)‐Catalyzed O‐Annulation of Cyclic Diazodicarbonyls with 2‐Naphthol, 6‐Quinolinol, β‐Tetralone, and 9‐Phenanthrol to Access Diverse Benzochromones

In(III)‐Catalyzed O‐Annulation of Cyclic Diazodicarbonyls with 2‐Naphthol, 6‐Quinolinol, β‐Tetralone, and 9‐Phenanthrol to Access Diverse Benzochromones

Visible‐Light Photoredox‐Catalyzed α‐Allylation of α‐Bromocarbonyl Compounds Using Allyltrimethylsilane

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