14790-34-2Relevant academic research and scientific papers
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.
