110599-23-0Relevant academic research and scientific papers
Metal-Free Formal Oxidative C?C Coupling by In Situ Generation of an Enolonium Species
Kaiser, Daniel,de la Torre, Aurélien,Shaaban, Saad,Maulide, Nuno
supporting information, p. 5921 - 5925 (2017/05/12)
Much contemporary organic synthesis relies on transformations that are driven by the intrinsic, so-called “natural”, polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well-known strategy, polarity reversal at the α-position of a carbonyl group is much rarer. Herein, we report the design of a novel electrophilic enolonium species and its application in efficient and chemoselective, metal-free oxidative C?C coupling.
Carbon-carbon bond-forming reactions of α-carbonyl carbocations: Exploration of a reversed-polarity equivalent of enolate chemistry
Lai, Ping-Shan,Dubland, Joshua A.,Sarwar, Mohammed G.,Chudzinski, Michael G.,Taylor, Mark S.
, p. 7586 - 7592 (2011/10/12)
Carbon-carbon bond-forming reactions of putative α-carbonyl carbocation intermediates generated by Lewis acid- or silver-promoted ionizations of toluenesulfonate or halide leaving groups are described. This under-exploited mode of reactivity represents an 'umpolung' of conventional enolate chemistry, and enables C-C bond construction in both intra- and intermolecular contexts. Attempts to develop diastereoselective variants of this process using chiral ester and oxazolidinone-based auxiliaries are discussed.
INTRA VS INTERMOLECULAR AMIDOALKILATION OF AROMATICS
Ishai, D. Ben,Sataty, I.,Peled, N.,Goldshare, R.
, p. 439 - 450 (2007/10/02)
Three tipes of intramolecular amidoalkylation reactions of aromatics, two endotrigonal and one exotrigonal (I, II, III), leading to indolone, N-acylisoquinolines, isoquinolone and benzazepinone derivatives were studied.In the presence of external aromatic nucleophiles competing intermolecular amidoalkylations were observed (1->2, 13->14).The mechanism and the synthetic limitations of the three types of cyclization is discussed.
