In Organic Chemistry by Clayden et al., the following reaction is shown:

Diastereoselective cyclopropanation of cyclohex-3-en-1-ol

The cyclopropane ring is formed on the same side as the alcohol group. Is this because of the interaction between Zn and the OH group, which directs the reagent to approach from the same side as the OH group?


Yes. Right after Clayden mentions this stereoselectivity, he proceeds to state that this is due to "coordination between the zinc atom and the hydroxyl group in the transition state" (pp. 1067-8, 1st ed):

enter image description here


Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.