Scale-Up of an Enantioselective
Overman Rearrangement for an Asymmetric Synthesis of a Glycine Transporter
1 Inhibitor
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Abstract
An enantioselective Overman 3,3-sigmatropic rearrangement
on a quinuclidine skeleton was developed for the pilot-plant synthesis
of a glycine transporter 1 inhibitor. The first stereocenter was produced
by a Ru-catalyzed asymmetric transfer hydrogenation process followed
by chirality transfer using the Overman rearrangement. The second
stereocenter was generated by a diastereoselective hydrogenation reaction