This short review focuses on enantiopure planar chiral [2.2]paracyclophanes (pCps), a fascinating class of molecules that possess an unusual threedimensional core and intriguing physicochemical properties. In the first part
Herein
we describe the desymmetrization of a centrosymmetric pseudo-para-diformyl[2.2]paracyclophane
based on Noyori asymmetric transfer hydrogenations (ATH). The reduction
proceeds smoothly in the presence of commercially available ruthenium
complexes to afford a monohydroxymethylated product in good yields
and excellent enantioselectivities (up to 74% isolated yield and 99%
ee). Our approach is operationally simple and can be run in gram-scale
without any significant loss in the reaction efficiency. This desymmetrization
strategy allows an easy access to an enantiopure compound bearing
on each aromatic ring of the pCp core different reactive groups suitable
for regioselective orthogonal postfunctionalization.
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