Asymmetric Synthesis of Tertiary Alcohols and Thiols via Nonstabilized Tertiary α-Oxy- and α-Thio-Substituted Organolithium Species
journal contributionposted on 2019-08-20, 12:03 authored by AP 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.
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.
CitationAngewandte Chemie International Edition, 2017, 56 (36), pp. 10835-10839
Author affiliation/Organisation/COLLEGE OF SCIENCE AND ENGINEERING/Department of Chemistry
- VoR (Version of Record)