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Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

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Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

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Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more...
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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Model studies directed toward the alkaloid mersicarpine utilizing a Rh(II)-catalyzed insertion/cycloaddition

Hao Li1, Sara A Bonderoff, Bo Cheng

  • 1Department of Chemistry, Emory University , Atlanta, Georgia 30322, United States.

The Journal of Organic Chemistry
|December 17, 2013
PubMed
Summary
This summary is machine-generated.

Researchers developed a rhodium(II)-catalyzed cascade reaction for synthesizing the alkaloid mersicarpine. This efficient method rapidly builds complex polycyclic structures with high stereoselectivity, forming key structural features of the target molecule.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • The alkaloid mersicarpine presents a complex polycyclic structure with multiple stereocenters.
  • Efficient synthetic routes are needed to access mersicarpine and its analogs for further study.

Purpose of the Study:

  • To develop a novel rhodium(II)-catalyzed cascade reaction for the synthesis of the alkaloid mersicarpine.
  • To construct the tricyclic core of mersicarpine with high yield and stereoselectivity.

Main Methods:

  • Rhodium(II)-catalyzed carbenoid insertion/cyclization/cycloaddition cascade reaction.
  • Utilized α-diazo dihydroindolinones as starting materials.
  • Acid-induced hydrolysis and subsequent multi-step transformations.

Main Results:

  • The cascade reaction of α-diazo dihydroindolinone 21 yielded cycloadduct 22 with high diastereoselectivity.
  • Successfully constructed the tricyclic core of mersicarpine.
  • The reaction rapidly assembled a polycyclic system with three new stereocenters and three continuous quaternary carbons.

Conclusions:

  • The developed cascade reaction is a powerful tool for the rapid and stereoselective synthesis of complex polycyclic systems.
  • This approach provides a viable route towards the synthesis of mersicarpine and related alkaloids.
  • Further steps involving reduction and reductive cyclization are planned for the synthesis of demethylmersicarpine.