New mono- and polyazafulleroids C-60(NR)(n) (n=1, 2, 4, 6) derived from a chiral azide containing N- and O-donor groups, and reactivity with [RhCl(CO)(2)](2)

Reactions in a 1:1 molar ratio of the chiral azide (2S,4S)-4-azido-1-benzyl oxycarbonyl-2-((t)butylaminocarbonyl)pyrrolidine (N3R, R = C17H23N2O3, 1) w ith C-60 in ClPh, in the temperature range 100- 132 degrees C, lead to mixt ures of mono- and polyazafulleroid species of general formula C-60(NR)(n) ( n = 1, 2, 4), with a composition depending on the reaction conditions, and with a yield in the most substituted polyazafulleroids that increases with the concentration of reactants. However the reaction in a 1:6 molar ratio ( fullerene-azide 1) leads only to hexaazafulleroids C-60(NR)(6). AU mono- an d polyazafulleroids C-60(NR)(n) react with [Rh(CO)(2)Cl](2) to give complex es of composition C-60(NR)(n)[Rh(CO)(2)Cl](n), which could be used as catal ysts in asymmetric hydrogenation of prochiral olefins. (C) 2000 Elsevier Sc ience S.A. All rights reserved.