Tetrahedron p. 11681 - 11692 (1995)
Update date:2022-08-03
Topics:
Shinokubo, Hiroshi
Miki, Hiroaki
Yokoo, Toshiaki
Oshima, Koichiro
Utimoto, Kiitiro
Stereospecific lithium-halogen exchange of alkenyl iodides was performed upon treatment with butyllithium in non-polar solvents such as hexane, benzene, and toluene at 25 deg C to provide alkenylllithiums quantitatively with retention of the configuration.Metal-iodine ecxhange of allenyl iodides with n-BuLi, i-PrMgBr or Et2Zn was also performed effectively to afford the corresponding allenylmetallic reagents.An addition of carbonyl compounds to the metallic reagents gave homopropargylic alcohols with high regioselectivity in good yields.
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