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Asymmetric Synthesis of Tertiary Alcohols and Thiols via Nonstabilized Tertiary α-Oxy- and α-Thio-Substituted Organolithium Species

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posted 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.

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

Version

  • VoR (Version of Record)

Published in

Angewandte Chemie International Edition

Publisher

Wiley for Gesellschaft Deutscher Chemiker (GDCh)

issn

1433-7851

Copyright date

2017

Available date

2019-08-20

Publisher version

https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201706722

Notes

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.

Language

en

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