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Updated: Feb 19, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

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P4O10/TfOH-アシストドワンポット アクセスで8オックスプロトーベルベリンにアクセス

Madhuri Gaikwad1, Hari Kadam1, Santosh Tilve1

  • 1School of Chemical Sciences, Goa University, Taleigao Plateau, Goa 403 206, India. stilve@unigoa.ac.in.

Organic & biomolecular chemistry
|February 17, 2026
PubMed
まとめ

研究者は,カスケードプロセスを用いて,8-オクソプロトベルベリンアルカロイドのための新しいワンポット合成を開発しました. この効率的な方法は,ジロピニンのような天然製品を含む多様な四環構造物へのアクセスを簡素化します.

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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