Fluoroallylboration-olefination for the synthesis of (Z)-4,4-difluoropent-2-enoates and 5,5-difluoro-5,6-dihydropyran-2-ones |
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| Authors: | Ramachandran P Veeraraghavan Tafelska-Kaczmarek Agnieszka Sakavuyi Kaumba Chatterjee Anamitra |
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| Institution: | Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, United States. chandran@purdue.edu |
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| Abstract: | Horner-Wadsworth-Emmons (HWE) or Still-Gennari olefination of TBS-protected 3,3-difluoro-4-hydroxy-2-ones, derived from the difluoroallylboration of aldehydes, provides the Z-isomer of 4,4,-difluoropent-2-enoates. These, upon hydrolysis, followed by Yamaguchi cyclization, afford 5,5-difluoro-4-methyl-5,6-dihydro-α-pyrones in high yields. |
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