A short asymmetric synthesis of methyl 2-((1S,3R)-3-((tert-butyldiphenylsilyl)oxy)cyclopentyl)acetate from norbornene

•Pd-(S)-MOP catalyzed hydrosilation of norbornene gives modest dr (84:16, exo/endo)•(S)-MOP catalyzed hydrosilation of norbornene gives 99%ee of exo and endo products.•(1R,4S)-stereochemistry is formed at the bridgehead carbons after oxidation.•Tandem oxidation/Baeyer-Villiger of norborneol leads to chiral bicyclic lactones.•The current route is competitive with established π-allyl desymmetrization methods.