79636-77-4Relevant articles and documents
Synthesis of new ethyl 9-methylene-13E and 13Z-retinoates via the Julia olefination reaction
Valla, Alain,Laurent, Alain,Prat, Virginie,Andriamialisoa, Zo,Cartier, Dominique,Giraud, Michel,Labia, Roger,Potier, Pierre
, p. 4795 - 4797 (2001)
Synthesis of new ethyl 9-methylene-13E and 13Z-retinoates via the 9-methylene C-15 sulphone 5 is reported. The Julia olefination strategy was used for building the C-20 skeleton.
The Cyclopropane Ring as a Reporter of Radical Leaving-Group Reactivity for Ni-Catalyzed C(sp3)-O Arylation
Mills, L. Reginald,Monteith, John J.,Dos Passos Gomes, Gabriel,Aspuru-Guzik, Alán,Rousseaux, Sophie A. L.
supporting information, p. 13246 - 13254 (2020/09/01)
The ability to understand and predict reactivity is essential for the development of new reactions. In the context of Ni-catalyzed C(sp3)-O functionalization, we have developed a unique strategy employing activated cyclopropanols to aid the design and optimization of a redox-active leaving group for C(sp3)-O arylation. In this chemistry, the cyclopropane ring acts as a reporter of leaving-group reactivity, since the ring-opened product is obtained under polar (2e) conditions, and the ring-closed product is obtained under radical (1e) conditions. Mechanistic studies demonstrate that the optimal leaving group is redox-active and are consistent with a Ni(I)/Ni(III) catalytic cycle. The optimized reaction conditions are also used to synthesize a number of arylcyclopropanes, which are valuable pharmaceutical motifs.
Synthesis of a cytotoxic vernolepin prototype. Ozonization of silyloxyalkenes
Clark,Heathcock
, p. 1396 - 1403 (2007/10/07)
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