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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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Stereoselective synthesis of optically active 3-hydroxy-7,8-dihydro-beta-ionol-glucosides

Yumiko Yamano1, Yuka Shimizu, Masayoshi Ito

  • 1Kobe Pharmaceutical University, Japan.

Chemical & Pharmaceutical Bulletin
|July 5, 2003
PubMed

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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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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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