Diastereoselective Ullmann Coupling to Bishelicenes by Surface Topochemistry

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Karl-Heinz Ernst published together with the Terfort group of Goethe University Frankfurt a paper in JACS entitled Diastereoselective Ullmann Coupling to Bishelicenes by Surface Topochemistry. Authors: A. Mairena, C. Wäckerlin, M. Wienke, K. Grenader, A. Terfort and K.-H. Ernst.

The comparison of the self-assembly 9,9’-bisheptahelicene on the Au(111) surface, studied with scanning tunneling microscopy, with the self-assembly of the same species obtained by on-surface synthesis via Ullmann coupling from 9-bromoheptahelicene reveals a diastereomeric excess for the (M,P)-meso-form of 50%. The stereoselectivity is explained by a topochemical effect, in which the surface-alignment of the starting material and the organometallic intermediate sterically favor the (M,P)-transition state over the homochiral transition states.

 

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