Stereoselective synthesis of substituted 2,5-diazabicyclo[2.2.1]heptanes by iodine-mediated cyclization of optically pure compounds containing the 4,5-diamino-1,7-octadiene and 1,2-diamino-4-alkene moieties

[摘要] 3,7-endo-Disubstituted 2,5-diazabicyclo[2.2.1]heptanes were obtained by iodo-cyclization of N,N'-di[(S)-1-phenylethyl]-(E,E)4,5-diamino-1,8-diphenyl-1,7-octadiene and substituted N,N'-di[(S)-1-phenylethyl]-1,2-diamino-4-alkenes. Removal of only one N-substituent of the bridged piperazines was achieved by reduction with ammonium formate and Pd/C. Unexpected cleavage of the skeleton of vinyl-substituted bridged piperazines was observed using hydrogen, leading to substituted 3-aminopyrrolidines. (c) 2007 Elsevier Ltd. All rights reserved.

[发布日期] 2007-12-10

[关键词] alkenes;cyclization;1,2-diamines;iodine;nitrogen heterocycles;piperazines