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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Gamma-hydroxynitrile alkylations: electrophile-dependent stereoselectivity.

Robert J Mycka1, Omar W Steward, Fraser F Fleming

  • 1Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530, USA.

Organic Letters
|June 8, 2010
PubMed
Summary

This study introduces a new method for creating quaternary centers in acyclic hydroxynitriles using chelation-controlled alkylations. The stereoselectivity of this process is tunable by modifying the electrophile and Grignard reagent.

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