π-Facial selectivities in nucleophilic additions to 4-hetero-tricyclo[5.2.1.02,6]decan-10-ones and 4-hetero-tricyclo[5.2.1.02,6]dec-8-en-10-ones: an experimental and computational study

Several endo-tricyclo[5.2.1.02,6]decan-10-ones and endo-tricyclo[5.2.1.02,6]dec-8-en-10-ones with hetero atom modifications at the distal C-4 position have been subjected to hydride reduction. π-Face selectivities in these systems are largely governed by the same electronic factors that were earlier identified in the case of the norbornyl system. A computational study demonstrates good predictability at the semi-empirical level.