Aluminacyclopentanes in the synthesis of ethyl 1-hydroxycyclopentanecarboxylates

Catalytic cyclometalation reaction of unsaturated compounds in synthesis of magnesa- and aluminacarbocycles

“…The reaction of generated in situ substituted aluminacyclopentanes with alkyl(phenyl)dichlorophosphines has been recognized as a convenient rout to transform a-olefins into phospholanes 77 [107][108][109]. Among known, the method for the synthesis of cyclopentanols 78 and 1-hydroxycyclopentanecarboxylates 79, which based on consecutive cycloalumination of a-olefins with trialkylalanes in the presence of Cp 2 ZrCl 2 catalyst via subsequent interaction between generated in situ aluminacyclopentanes and alkyl carboxylates in the presence of catalytic amounts of Cu, Ni, Pd salts or complexes is considered to be the most attractive [107,[110][111][112]. The elaborated method has been successfully applied to the synthesis of secondary and tertiary alcohols via the interaction between generated in situ 1-ethyl-3-alkylaluminacyclopentanes 31 at 20°C and aldehydes or ketones in the presence of catalytic amounts of Cu salts.…”