Chemistry Commons^™

Asymmetric Cuh-Catalyzed Reductive Coupling Of Allenamides With Carbonyl And Imine Electrophiles, Stephen Collins

Theses and Dissertations

The carbon scaffold of many drugs and natural products contain multiple stereogenic centers bearing heteroatoms. As a result of this, chemists have long sought methods to efficiently install these multi-heteroatom functionalities. Reductive coupling reactions have been extensively studied over the past decades, and the allylation of carbonyls via the reductive coupling approach has been a key method for generating chiral allylic alcohols. This work utilizes inexpensive Cu for the asymmetric reductive coupling of allenamides with carbonyls or imines to simultaneously install two heteroatoms (either oxygen and nitrogen or nitrogen and nitrogen, respectively) onto the product. These molecules have a polarity …