posted on 2019-08-20, 12:03authored byAP Pulis, A Varela, C Citti, P Songara, D Leonori, VK Aggarwal
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.
Funding
We thank the University of Manchester (Lectureship to A.P.P.), the EPSRC (EP/I038071/1), and the EPSRC‐funded Bristol Chemical Synthesis Centre for Doctoral Training (EP/G036764/1) for financial support. We also thank Siying Zhong and Ikenna Ndukwe for NMR studies to determine the stereochemistry of compound 9.
History
Citation
Angewandte Chemie International Edition, 2017, 56 (36), pp. 10835-10839
Author affiliation
/Organisation/COLLEGE OF SCIENCE AND ENGINEERING/Department of Chemistry
Supporting information and the ORCID identification number(s) for
the author(s) of this article can be found under:
https://doi.org/10.1002/anie.201706722.