Development of novel cyclopropylaminophosphine ligands for transition metal catalysis in carbon dioxide-expanded solvents

ORGN 482

Michael Rubin, mrubin@ku.edu and William M. Sherrill, Mwampoki@bigfoot.com. Department of Chemistry, Universtity of Kansas, 1251 Wescoe Hall Drive, RM 5088, Malott Hall, Lawrence, KS 66045
A modular approach to novel cyclopropane-containing C1-symmetric chiral aminophosphine ligands has been developed. This approach allows for the facile installation of various N- and P-containing substituents in the side chain of cyclopropane with complete control of all chiral centers in the cyclopropyl backbone at several key steps in the synthesis. Complementary routes will be shown for obtaining the cis- and trans-ligands, with the stereochemistry in respect to the amino and phospanyl groups, from readily accessible cyclopropylcarboxylates. Application of the new chiral ligands in asymmetric transition metal-catalyzed transformations will be discussed.