We thank EPSRC for funding, the Swiss National Foundation for a fellowship (L.C.B.), the University of Bristol for a Post-Graduate Scholarship (A.P.P.), the EPSRC-funded Bristol Chemical Synthesis Doctoral Training Centre for a PhD studentship (M.B.), Inochem-Frontier Scientific for their generous donation of boronic acids and esters, Dr. Mairi Haddow for X-ray analysis, and R. Sanguramath for help in making metal–allene complexes.
Enantioselective Synthesis and Cross-Coupling of Tertiary Propargylic Boronic Esters Using Lithiation–Borylation of Propargylic Carbamates†
Article first published online: 17 OCT 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 47, pages 11795–11799, November 19, 2012
How to Cite
Partridge, B. M., Chausset-Boissarie, L., Burns, M., Pulis, A. P. and Aggarwal, V. K. (2012), Enantioselective Synthesis and Cross-Coupling of Tertiary Propargylic Boronic Esters Using Lithiation–Borylation of Propargylic Carbamates . Angew. Chem. Int. Ed., 51: 11795–11799. doi: 10.1002/anie.201203198
- Issue published online: 14 NOV 2012
- Article first published online: 17 OCT 2012
- Manuscript Received: 25 APR 2012
- boronic esters;
- propargylic alcohols
Lithiation–borylation of propargylic carbamates leads to tertiary propargylic boronic esters in very high e.r., provided that ethylene glycol boronic esters are used. These versatile intermediates undergo a range of highly stereoselective transformations, including protodeboronation to give tertiary allenes and Suzuki–Miyaura cross-couplings of tertiary boron species leading to tetrasubstituted allenes with high enantiospecificity.