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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