Abstract
The stereoselective conjugate addition reaction of organolithium reagents to unprotected 4hydroxycyclopentenones is reported. The OH group on the substrate is transformed into the corresponding magnesium alkoxide, which has been used to control the regioselectivity of the organolithium addition. Following this procedure, the conjugate addition reaction was obtained instead of the products of direct addition to the carbonyl group usually found in other organolithium additions to similar starting materials. Additionally, the OH group controls the cisstereochemistry of the final products. Both aspects, regioand stereoselectivity, can be understood by means of a chelation-controlled addition.
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