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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Indium-mediated regio- and diastereoselective reduction of norbornyl alpha-diketones

Faiz Ahmed Khan1, Jyotirmayee Dash, Ch Sudheer

  • 1Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India. faiz@iitk.ac.in

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 18, 2004
PubMed

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Carboxylic Acids to Primary Alcohols: Hydride Reduction

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Acid Halides to Alcohols: LiAlH4 Reduction

Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
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Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
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