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Nonstabilized α-O-substituted tertiary organolithium species are difficult to generate, and the α-S-substituted analogues are configurationally unstable. We now report that they can both be generated easily and trapped with a range of electrophiles with high enantioselectivity, providing ready access to a range of enantioenriched tertiary alcohols and thiols. The configurational stability of the α-S-organolithium species was enhanced by using a less coordinating solvent and short reaction times.
- BCS and TECS CDTs
Pulis, A., Varela, A., Citti, C., Songara, P., Leonori, D., & Aggarwal, V. (2017). Asymmetric Synthesis of Tertiary Alcohols and Thiols via Nonstabilized Tertiary a-Oxy- and a-Thio-Substituted Organolithium Species. Angewandte Chemie - International Edition, 56(36), 10835-10839. https://doi.org/10.1002/anie.201706722