Projects per year
Abstract
Enantioenriched secondary and tertiary alkyl pinacolboronic esters undergo enantiospecific deborylative alkynylation through a Zweifel-type alkenylation followed by a 1,2-elimination reaction. The process involves the use of α-lithio vinyl bromide or vinyl carbamate, species whose application to Zweifel-type reactions has not previously been explored. The resulting functionalized 1,1-disubstituted alkenes undergo facile base-mediated elimination to generate the terminal alkyne products in high yield and excellent levels of enantiospecificity over a wide range of pinacolboronic ester substrates. Furthermore, we have demonstrated that, in addition to terminal alkynes, internal and silyl-protected alkynes can be formed by simply introducing a suitable carbon- or silicon-based electrophile after the base-mediated 1,2-elimination reaction
Original language | English |
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Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 55 |
Issue number | 13 |
Early online date | 2 Mar 2016 |
DOIs | |
Publication status | Published - 18 Mar 2016 |
Keywords
- alkynes
- boronic esters
- alkynylation
- synthetic methods
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Projects
- 3 Finished
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Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
14/05/12 → 13/01/18
Project: Research
Profiles
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Professor Varinder K Aggarwal
- School of Chemistry - Alfred Capper Pass Chair of Chemistry
- Synthesis
- Supramolecular and Mechanistic Chemistry
- Catalysis
Person: Academic , Member