Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes

Hengbin Wang, David M. Guptill, Adrián Varela-Álvarez, Djamaladdin G. Musaev, Huw M. L. Davies

Chemical Science,
2013, 2844-2850; 10.1039/C3SC50425E


This collaborative project between the Davies and Musaev groups grew out of a project that was begun in the Davies group outside of the Centers remit.

During the synthesis of chiral cyclopropanes it was identified that there was some unusual mechanistic features in play. Through a combination of experimental and theoretical studies it was elucidated that the carbene can form a reversible ylide intermediate during the reaction, which can then act as a directing group for reaction.

These finding have significant implications for future applications of dirhodium-catalyzed carbene transformations, including C-H Functionalization. manifold.

Related Content