75412-18-9Relevant academic research and scientific papers
Stereospecific Cross Couplings to Set Benzylic, All-Carbon Quaternary Stereocenters in High Enantiopurity
Zhou, Qi,Cobb, Kelsey M.,Tan, Tianyu,Watson, Mary P.
, p. 12057 - 12060 (2016)
Asymmetric preparation of all-carbon quaternary stereocenters is an important goal. Despite advances in formation of highly enantioenriched products with quaternary stereocenters proximal to a functional group, methods to install quaternary stereocenters isolated from functional groups are limited. Transition metal catalysis offers a potential solution, but prior cross couplings are limited to allylic substrates or deliver little to no enantiomeric enrichment. We report a stereospecific, nickel-catalyzed Suzuki-Miyaura arylation of tertiary benzylic acetates to deliver products with diaryl and triaryl quaternary stereocenters in high yields and ee's. This reaction employs an inexpensive, air-stable Ni(II) salt and commercially available phosphine ligand to transform tertiary alcohol derivatives, which are easily available in exceptional ee, into valuable products with stereoretention.
