Literature DB >> 21988178

Copper-catalyzed enantioselective additions to oxocarbenium ions: alkynylation of isochroman acetals.

Prantik Maity1, Harathi D Srinivas, Mary P Watson.   

Abstract

We have developed an enantioselective, copper(I)-catalyzed addition of terminal alkynes to racemic isochroman acetals. This method is one of the first transition-metal-catalyzed approaches to enantioselective additions to prochiral oxocarbenium ions. In this reaction, TMSOTf is used to form the oxocarbenium ion in situ under conditions compatible with simultaneous formation of the chiral copper acetylide. By using a bis(oxazoline) ligand, good yields and enantioselectivities are observed for a variety of enantioenriched 1-alkynyl isochromans.

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Year:  2011        PMID： 21988178      PMCID： PMC4203715          DOI： 10.1021/ja207585p

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  33 in total

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  19 in total

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10.  Enantioselective Allylic C-H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis.

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