1998
DOI: 10.1021/jo9807159
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An Efficient Stereoselective Synthesis of Fluorinated Trisubstituted Alkenes

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Cited by 30 publications
(12 citation statements)
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“…A very efficient 2-fluoroacrylate ester synthesis is based on a domino reaction where the first step is the addition of fluoromalonate to an -unsaturated ketone followed by elimination to give a fluoroacrylate derivative. 44 Although the yields vary from poor to excellent, the E/Z selectivity of the reaction is very good (Scheme 11). SCHEME 11.…”
Section: Reactions With Carbon Electrophilesmentioning
confidence: 99%
“…A very efficient 2-fluoroacrylate ester synthesis is based on a domino reaction where the first step is the addition of fluoromalonate to an -unsaturated ketone followed by elimination to give a fluoroacrylate derivative. 44 Although the yields vary from poor to excellent, the E/Z selectivity of the reaction is very good (Scheme 11). SCHEME 11.…”
Section: Reactions With Carbon Electrophilesmentioning
confidence: 99%
“…Therefore, new stereoselective methods for generating trisubstituted olefins remains an ongoing challenge in the area of synthetic organic chemistry. A wide variety of methods have been investigated to date including intramolecular Claisen rearrangments, , Wittig olefination, Julia couplings, Peterson olefination, alkylation of sulfonyl hydrazones, and direct methods for the preparation of flourinated trisubstituted alkenes . Transition metal mediated routes including hydromagnesization, hydrozirconation, and the use of organocuprates have also been reported but often suffer from use of harsh stoichiometric reagents.…”
mentioning
confidence: 99%
“…− MS (EI); m / z (%): 165 (100) [M + − t Bu] [found (HRMS, FAB) for [M + ] 182.1665, C 12 H 22 O requires 182.1671]. − Compound 5c has been described in the literature25,26 but no spectroscopic or physical data were reported 27…”
Section: Methodsmentioning
confidence: 99%