Cyclic vinylogous triflate hemiacetals as new surrogates for alkynyl aldehydes |
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Authors: | Shin Kamijo |
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Institution: | Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA |
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Abstract: | Cyclic vinylogous triflate hemiacetals can serve as ‘synthetic equivalents’ for alkynyl aldehydes: treatment of a vinylogous triflate hemiacetal with excess amounts of Grignard reagents produces acyclic alkynyl alcohols in good to high yields. This transformation likely involves the Grob-type C-C bond cleaving fragmentation to form the alkynyl aldehyde in situ. Subsequent nucleophilic attack of the Grignard reagent furnishes secondary alkynols. Vinylogous triflate hemiacetals are easily prepared by DIBALH reduction of vinylogous acyl triflates, which are derived from cyclic 1,3-diketones. |
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Keywords: | Alkynyl aldehyde surrogate C-C bond cleavage Grignard reagent Vinylogous acyl triflate Vinylogous triflate hemiacetal |
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