American Chemical Society
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Regioselective Allylmetalation of Allenes with Tetraallylmanganate or Allylmagnesium Chloride under MnCl2 Catalysis

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journal contribution
posted on 2003-11-27, 00:00 authored by Toshihiro Nishikawa, Hiroshi Shinokubo, Koichiro Oshima
Treatment of allenes with tetraallylmanganate provides allylated products with high regioselectivity. A catalytic amount of MnCl2 combined with allylmagnesium chloride also achieves efficient allylmetalation of allenes. The resulting alkenylmagnesium species react with various electrophiles. In the presence of molecular oxygen, the alkenylmagnesium undergoes diallylation reaction. A cyclization reaction of 1,2,6-heptatriene with tetraallylmanganate is also described.