Catalytic enantioselective synthesis of quaternary carbon stereocentres

Carbon atoms to which four distinct carbon substituents are attached — quaternary carbon stereocentres — are common features of molecules found in nature; in this Review, the authors discuss catalytic enantioselective reactions that have been developed during the past decade for synthesizing organic molecules containing such carbon atoms. Carbon atoms with four distinct carbon substituents attached — known as quaternary stereocentres — are found in many biologically active natural products, such as cortisone and morphine. This important structural motif has proved a challenge to synthetic chemists and until recently there were few methods available for its construction. Here Kyle Quasdorf and Larry Overman discuss the catalytic enantioselective reactions that have been developed during the past decade for synthesizing organic molecules containing quaternary stereocentres. The methods now available remove much of the previous barrier to incorporating quaternary stereocentres in organic molecules for use in medicine, agriculture and other areas. Quaternary carbon stereocentres—carbon atoms to which four distinct carbon substituents are attached—are common features of molecules found in nature. However, before recent advances in chemical catalysis, there were few methods of constructing single stereoisomers of this important structural motif. Here we discuss the many catalytic enantioselective reactions developed during the past decade for the synthesis of single stereoisomers of such organic molecules. This progress now makes it possible to incorporate quaternary stereocentres selectively in many organic molecules that are useful in medicine, agriculture and potentially other areas such as flavouring, fragrances and materials.