Direct Catalytic Asymmetric Synthesis of α-Chiral Bicyclo[1.1.1]pentanes
Edward Anderson and Fernanda Duarte synthesized α-chiral bicyclo[1.1.1]pentanes.
Bicyclo[1.1.1]pentanes (BCPs) have become highly attractive bioisosteres for para-substituted arenes and tert-butyl groups in medicinal chemistry, due to their advantageous pharmaco-kinetic properties. However, the synthesis of BCPs featuring adjacent stereocenters has remained a significant challenge – these motifs would correspond to α-stereogenic benzyl groups, which are again of high importance in drug design. The group of Professor Edward A. Anderson at the University of Oxford (UK) has been studying this area for some time. They were looking for new ways to install an α-stereocenter on a pre- formed BCP and worked on the direct formation of a stereogenic center upon ring-opening of [1.1.1]propellane. Collaborating with the group of Professor Fernanda Duarte from the same university revealed interesting insights on the reaction mechanism.
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