摘要:
Atom transfer radical cyclization of N-(alpha-methyl)benzyl substituted trichloroacetamide upon alpha,beta-unsaturated nitriles in compounds 1, using Cud, trispyridylmethylamine (TPMA), and AIBN as a reducing agent, gives morphan derivatives (2 and 3) and the unusual normorphans 4 and 5, as well as the unexpected azaspirodecanes 6. Stereospecific formation of normorphans involves memory of chirality in the cyclization step and azaspirodecanes are generated by a radical dearomative ipsocyclization followed by a radical dimerization. (C) 2013 Elsevier Ltd. All rights reserved.