All-Carbon Quaternary Centers via Catalytic Asymmetric Hydrovinylation

Significance

The highly enantioselective construction of an all-carbon stereocenter at the benzyl position has been accomplished. Using nickel catalysis with phosphoramidite ligand 1, the authors achieved high yields (over 90% in most cases), high selectivities (>95% for the benzyl position) and high ee values (>90% in most cases). The reaction proceeds at low temperature (-60 °C to -70 °C) and is complete within 4-14 hours. The use of ethylene as the vinyl source is also extrememly efficient.