SYNTHESIS OF ENANTIOPURE NORBORNANE DERIVATIVES - EFFECT OF BRIDGEHEAD SUBSTITUENT ON THE PI-FACIAL SELECTIVITY OF THE REDUCTION OF 2-NORBORNANONES AND THEIR OXIMES

One of the most important features of the synthesis of camphor-derived compounds is the control of the stereochemistry at the C2 position. A ccording to this, reduction of bridgehead-substituted 2-norbornanones 1 and 2-norbornanoximes 3 has been considered by us as a very convenie nt method for the preparation of different classes of enantiomerically pure 1,2- and 1,3-difunctionalised norbornane derivatives. Factors co ntrolling the stereoselectivity in these reductions, as well as the ro le played by the nature of the bridgehead functional groups are discus sed. (C) 1998 Elsevier Science Ltd. All rights reserved.