Diastereo- and Enantioselective Conjunctive Cross-Coupling via a Metalate Shift

Key words

palladium catalysis - conjunctive cross-coupling - metalate shift

Significance

The authors describe a conjunctive cross-coupling process to access products with vicinal stereogenic centers. This method avoids the generation of Suzuki–Miyaura stilbene byproducts obtained when typical boronic esters are employed.

Comment

Products are obtained in moderate yields and excellent enantio- and diastereoselectivities. The synthetic utility of the –B(mac) handle is demonstrated. Additionally, this methodology was used for the synthesis of (+)-obtusafuran.