Acetoxyl group directed cyclization promoted by SmI2: directing group determined stereocomplementarity.
Complete reversal of diastereoselectivity was observed in the SmI(2)-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI(2)-induced ketyl-olefin coupling cyclizations of the delta-hydroxy ketone 1 and delta-acetoxy ketone 3.
Kan
Toshiyuki
T
Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan.
Hosokawa
Seijiro
S
Nara
Shinji
S
Tamiya
Hiroaki
H
Shirahama
Haruhisa
H
Matsuda
Fuyuhiko
F