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Seminar

Department of Chemistry
Indian Institute of Technology Delhi

Copper(I) Catalysis of Oxocarbenium Ions

Dr Prantik Maity

University of Delaware, Department of Chemistry & Biochemistry, 401 Academy Street, Newark, DE, 19716

Date : March 8th 2013 (Friday)
Time : 4:00 pm
Venue: Committee Room, Chemistry Department


We have developed an enantioselective, copper(I)-catalyzed addition of terminal alkynes to racemic isochroman acetals. This method is one of the first transition-metalcatalyzed 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.

We have developed a nickel-catalyzed cross coupling of benzylic ammonium trifl ates with aryl boronic acids to aff ord diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent chirality transfer, off ering a new strategy for the synthesis of highly enantioenriched diarylethanes from readily available chiral benzylic amines.

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Department of Chemistry, Indian Institute of Technology Delhi