Asymmetric Hydroformylation of an Enantiomerically Pure Bicyclic Lactam: Efficient Synthesis of Functionalised Cyclopentylamines

摘要

Customising a bicycle: Rh-catalysed asymmetric hydroformylation of a bicyclic lactam, 2-azabicyclo-[2.2.1]hept-5-en-3-one, was investigated. The use of a chiral diphosphite ligand, (R,R)-Kelliphite, enables excellent selectivity towards one regioisomer combined with excellent productivity and perfect exo selectivity. The products are versatile precursors to highly desired functionationalised cyclopentylamines (see scheme).