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Copper catalysed conjugate addition of Grignard reagents to 2-silyloxycyclohexene carboxylates in the presence of an excess chlorotrimethylsilane, leads diastereoselectively to related (anti) (Z) silylketene acetals. Subsequent hydrolysis and desilylation afford 2-hydroxycyclohexane carboxylates in high yields and diastereoselectivities.
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 SN 2 reaction by-products. No loss of selectivity is also observed when a catalytic amount of cuprous salt is used.
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