Cu-Mediated Rearrangements of Allenylcyclopropanols to Cyclopentenones: Two Divergent Pathways.
Two CuCN-mediated rearrangement reactions of allenylcyclopropanols to cyclopentenones have been achieved by means of Et2Zn/CuCN·2LiCl or CuCN·2LiCl to afford 5-alkyl or 4-alkyl cyclopentenone regioisomers: the former conditions afford 5-alkyl substituted cyclopentenones via β-carbon elimination, whereas the latter result in the 4-alkyl substituted regioisomers with concomitant oxidation at the γ-position, via a free radical mechanism.
Department of Chemistry, Wayne State University , 5101 Cass Ave, Detroit, Michigan 48202, United States.
Naresh
N
Tumma
Department of Chemistry, Wayne State University , 5101 Cass Ave, Detroit, Michigan 48202, United States.
Eppa
E
Gyanchander
Department of Chemistry, Wayne State University , 5101 Cass Ave, Detroit, Michigan 48202, United States.
Jin Kun
0000-0003-4038-3213
JK
Cha