Vicinal epoxymesylates: Substrates for iterative organocuprate chemistry

Article abstract of DOI:10.1016/S0040-4020(01)87815-7

Reacting vicinal epoxymesylates of general structure i with higher order and mixed higher order organocuprate reagents is shown to be very selective for attack at the least hindered epoxide center. The iterative application of this reaction - a sequence which consists of cuprate opening of epoxide i, reformation of an epoxide (I→ii), and subsequent cuprate opening of this intermediate epoxide (ii→iii) - provides ready access to acyclic carbon frameworks with up to three contiguous stereogenic centers.