Projects per year
Abstract
The coupling of ortho- and para-phenols with secondary and tertiary boronic esters has been explored. In the case of para-substituted phenols, after reaction of a dilithio phenolate species with a boronic ester, treatment with Ph3BiF2 or Martin's sulfurane gave the coupled product with complete enantiospecificity. The methodology was applied to the synthesis of the broad spectrum antibacterial natural product (−)-4-(1,5-dimethylhex-4-enyl)-2-methyl phenol. For ortho-substituted phenols, initial incorporation of a benzotriazole on the phenol oxygen atom was required. Subsequent ortho-lithiation and borylation gave the coupled product, again with complete stereospecificity.
Original language | English |
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Pages (from-to) | 16318-16322 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 56 |
Issue number | 51 |
Early online date | 28 Nov 2017 |
DOIs | |
Publication status | Published - 18 Dec 2017 |
Keywords
- arylation
- boronic esters
- C−C bond formation
- phenol
- synthetic methods
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Dive into the research topics of 'Enantiospecific sp2–sp3 Coupling of ortho- and para-Phenols with Secondary and Tertiary Boronic Esters'. Together they form a unique fingerprint.Projects
- 3 Finished
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FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds
Aggarwal, V. K. (Principal Investigator)
1/10/15 → 31/03/21
Project: Research
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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
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Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K. (Principal Investigator)
14/05/12 → 13/01/18
Project: Research