Copper(I) mediated highly diastereoselective conjugate addition of Grignard reagents to 2-silyloxycyclopentenecarboxylates

Article abstract of DOI:10.1016/0040-4039(96)01386-X

The conjugate addition of magnesium cuprates to 2-silyloxycyclopentenecarboxylates leads, after desilylation, to 5-substituted-2-hydroxycyclopentanecarboxylates in high yields and diastereoselectivities. The 2-silyloxy derivatives avoid the formation of the SN₂' reaction by-products. No loss of selectivity is also observed when a catalytic amount of cuprous salt is used.