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Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes |
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| Authors: | Idris Karakaya Semistan Karabuga Ramazan Altundas Sabri Ulukanli |
| Institution: | 1. Department of Chemistry, Faculty of Science and Letters, Osmaniye Korkut Ata University, 80000 Osmaniye, Turkey;2. Department of Chemistry, Faculty of Science and Letters, Kahramanmaras Sutcu Imam University, 46100 Kahramanmaras, Turkey;3. Department of Chemistry, Faculty of Science, Ataturk University, 25240 Erzurum, Turkey |
| Abstract: | Five novel 4-phenylquinazolinols were synthesised in three steps. Their application as ligands in the titanium tetraisopropoxide promoted catalytic enantioselective addition of phenylacetylene to a variety of aldehydes gave propargylic alcohols. Under the optimised reaction conditions, the best enantioselectivity was obtained using l-lactic acid derived 4-phenylquinazolinol and apart from the cyclohexylcarbaldehyde derivative, 16 propargylic alcohols were then synthesised in moderate to excellent enantiomeric excess from 53% to 97%. |
| Keywords: | Quinazolines Quinazolinones Phenylacetylene Asymmetric alkynylation Propargylic alcohol Diethylzinc and organozinc addition |
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