Abstract
Addition of propargylic or homopropargylic ynols to dicobalt hexacarbonyl propargylium cations gave the expected ether products of the Nicholas reaction, with the exception of 4-phenyl-3-butyn-1-ol which gave a dihydrofuran due to propargylium cation promoted 5-endo ring-closure. Use of chiral dicobalt hexacarbonyl complexed propargylic ynols as both propargylium cation precursor and nucleophile gave racemic doubly complexed disymmetric diyne ethers, each as a single diastereoisomer. Addition of dicobalt hexacarbonyl complexed 1-phenyl-1-butyne-3-ene to the propargylium cation derived from dicobalt hexacarbonyl complexed 1-phenyl-1-butyn-3-ol, followed by the addition of a nucleophile (NuH), gave double complexed 1,7-diphenyl-3-Nu-5-methylhepta-1,6-diynes (d.r. > 10:1).
Original language | English |
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Pages (from-to) | 43-50 |
Number of pages | 8 |
Journal | Journal of Organometallic Chemistry |
Volume | 776 |
Early online date | 31 Oct 2014 |
DOIs | |
Publication status | Published - 15 Jan 2015 |
Keywords
- Alkynes
- Cobalt
- Ethers
- Cations
- Diastereoselective