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Enantio- and Diastereoselective Suzuki-Miyaura Coupling with Racemic Bicycles
preprintsubmitted on 23.05.2019, 16:32 and posted on 24.05.2019, 15:32 by Friedrich Wieland Goetzke, Mike Mortimore, Stephen P. Fletcher
Herein we describe a rhodium-catalyzed enantio- and diastereoselective Suzuki-Miyaura cross-coupling between racemic fused bicyclic allylic chlorides and boronic acids. The highly stereoselective transformation allows for the coupling of aryl-, heteroaryl- and vinyl boronic acids and gives access to functionalized bicyclic cyclopentenes which can be converted to other five-membered ring scaffolds with up to five contiguous stereocenters. Preliminary mechanistic studies suggest that these reactions occur with overall retention of the relative stereochemistry and is enantioconvergent for pseudo-symmetric allylic chloride starting materials. In addition, a bicyclic allylic chloride starting material without pseudo-symmetry undergoes a highly enantioselective regiodivergent reaction.
Read the published paper
in Angewandte Chemie