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for a similar Inflating agent see: D. L. Comins, A. Dehghani, Tetrahedron Lett. 1992, 33, 6229-6302;
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or a short review on the reagent see: b R. Zimmer, M. Webel, H.-U. Reißig, J. Prakt. Chem. 1998, 340, 274-277.
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or a short review on the reagent see: b) R. Zimmer, M. Webel, H.-U. Reißig, J. Prakt. Chem. 1998, 340, 274-277.
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0001768002
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For a comparison in reactivity of aryl Inflates and nonaflates in Negishi couplings see
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We recently found that alkenyl nonaflates of 8-oxabicyclo-[3.2.1]octan-3- ones show a slightly higher reactivity in Heck, Suzuki and Sonogashira reactions. J. Högermeier, Dissertation, Freie Universität Berlin, 2006
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We recently found that alkenyl nonaflates of 8-oxabicyclo-[3.2.1]octan-3- ones show a slightly higher reactivity in Heck, Suzuki and Sonogashira reactions. J. Högermeier, Dissertation, Freie Universität Berlin, 2006.
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34250681869
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These conditions were examined earlier in our laboratory (M. Webel, Dissertation, Technische Universität Dresden, 2000). Here 1-cyclopentenyl nonaflate was used which can not undergo fragmentation. However, yields were moderate as coupling of this nonaflate with 4-methoxyphenyl boronic acid furnished 1-(4-methoxyphenyl)-cyclopentene in only 53 % yield.
-
These conditions were examined earlier in our laboratory (M. Webel, Dissertation, Technische Universität Dresden, 2000). Here 1-cyclopentenyl nonaflate was used which can not undergo fragmentation. However, yields were moderate as coupling of this nonaflate with 4-methoxyphenyl boronic acid furnished 1-(4-methoxyphenyl)-cyclopentene in only 53 % yield.
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42
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34250653716
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3-mediated cleavage of a highly substituted cycloheptyl ring derived from an 8-oxabicylo[3.2.1]octenone was used by Lautens for the synthesis of callistatin A: a M. Lautens, T. A. Stammers, Synthesis 2002, 1993-2012;
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Deprotonations of bicyclic ketones were carried out by using lithium (R.R′)-bis(1-phenylethyl)amide as a chiral base. We also showed that no decrease of the ee is observed in the Suzuki reactions which use enantioenriched nonaflates. J. Högermeier, Dissertation, Freie Universität Berlin, 2006. A manuscript further discussing the enantioselective synthesis of bicyclic alkenyl nonaflates is currently in preparation.
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Deprotonations of bicyclic ketones were carried out by using lithium (R.R′)-bis(1-phenylethyl)amide as a chiral base. We also showed that no decrease of the ee is observed in the Suzuki reactions which use enantioenriched nonaflates. J. Högermeier, Dissertation, Freie Universität Berlin, 2006. A manuscript further discussing the enantioselective synthesis of bicyclic alkenyl nonaflates is currently in preparation.
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