Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5219802 | Tetrahedron | 2011 | 7 Pages |
Abstract
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.
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Chemistry
Organic Chemistry
Authors
Ping-Shan Lai, Joshua A. Dubland, Mohammed G. Sarwar, Michael G. Chudzinski, Mark S. Taylor,