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Stereospecific conversion of alcohols into pinacol boronic esters using lithiation–borylation methodology with pinacolborane

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posted on 02.10.2019, 15:21 by S Roesner, CA Brown, M Mohiti, AP Pulis, R Rasappan, DJ Blair, S Essafi, D Leonori, VK Aggarwal
The synthesis of primary and secondary pinacol boronic esters via lithiation–borylation of carbamates and benzoates with pinacolborane is described. This new protocol enables the highly selective synthesis of enantioenriched and geometrically defined boronic esters that cannot otherwise be accessed by alternative methodologies.

Funding

We thank EPSRC and the European Research Council (FP7/2007-2013, ERC grant no. 246785) for support. R. R. thanks the Marie Curie Fellowship program (EC FP7, no. 329578).

History

Citation

Chemical Communications, 2014, 50 (31), pp. 4053-4055

Author affiliation

/Organisation/COLLEGE OF SCIENCE AND ENGINEERING/Department of Chemistry

Version

VoR (Version of Record)

Published in

Chemical Communications

Publisher

Royal Society of Chemistry

issn

1359-7345

eissn

1364-548X

Acceptance date

26/02/2014

Copyright date

2014

Available date

02/10/2019

Publisher version

https://pubs.rsc.org/en/content/articlelanding/2014/CC/C4CC00993B#!divAbstract

Notes

Electronic supplementary information (ESI) available: Detailed experimental procedures, 1 H and 13C NMR spectra of all new compounds, chiral HPLC and SFC traces. See DOI: 10.1039/c4cc00993b

Language

en

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