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![]() Kong, K.; Moussa, Z.; Romo, D. Org. Lett. 2005, 7, 5127-5130. "In Ke Kong's journal article, Kong explains his ambition to discover an enantiosynthesis of the spirocyclic imine (-)-gymnodimine (a marine toxin) in order to provide modern antigens to monitor and eliminate it. Preliminary trials to promote this Diels-Alder enantioselective reaction failed with the diene (Z)-silylenol ether due to a lack of reactivity, even in the presence of chiral catalysts. This failed reactivity was most likely attributed to geometrical issues so the synthesis of the diene (E)-silylenol ether (which is our product 24) was pursued. In the first step for (E)-silylenol ether's synthesis, (E)-vinyl stannane was used as a starting material rather than other radical and metal-catalyzed hydrostannylations because its regioselectivity was more stable and therefore formed the final (E)- silylenol ether. (E)-vinyl stannane goes through tin-lithium exchange with n-BuLi followed by a reaction with the amide N-methyl-N-methoxyacetamide in order to form the ketone (which is our intermediate S-6). This essentially describes the first step for the formation of (E)- silylenol ether; the ketone continues through enolization and silyation to form (E)- silylenol ether.
Comparing References - 3 articles that cite the above article:
3 articles that cited the above: 1) Wolf C.; Xu H. Chem. Commun. 2011, 47, 3319-3350. 2) Ma, M.; Lu, R.; Pullarkat, S. A.; Deng, W.; Leung, P. Dalton Trans. 2010, 39, 5453-5461. 3) Jones, A. L.; Snyder, J. K. Org. Letter. 2010, 12, 1592-1595. |
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